


Harem Master Ash

by Sinfulnature1123



Category: Pocket Monsters | Pokemon (Anime)
Genre: Blackmail, Dominance, Futanari, Harems, Masochism, Mind Games, Non-Consensual Body Modification, Pokephilia, Rape/Non-con Elements, Rough Sex, Watersports
Language: English
Status: Completed
Published: 2020-06-05
Updated: 2021-02-19
Packaged: 2021-03-03 19:22:13
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 18
Words: 32,655
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24560746
Author URL: https://archiveofourown.org/users/Sinfulnature1123/pseuds/Sinfulnature1123
Summary: Requested novel fanfic story. Ash has been raised under the perfect circumstances to make him an unstoppable harem master.
Comments: 1
Kudos: 117





	1. Chapter 1

Ash woke in his bed, yawning softly as he rose. 

As he moved, he noticed and remembered the woman laying naked at either side of him. He brought his hands down hard on both of their already presented asses, the sound of the smack followed by their soft groans of delight. 

“Up and at it, it's morning.” Ash ordered with a smiled. 

The women nodded, getting shakily out of bed and onto their feet on shaky legs. Their movement was more than a little off as they moved to leave the room, both from the slight limp the previous night had left them with and from their attempts to avoid making too much of a mess with the seed dripping slowly from between their legs. 

Ash stretched out, and got up to go about his day as well. The boy had always had an interesting life, and it had been his mothers to thank for it. Delia had just been another happy woman going about her life in the big city of Celadon. 

When her husband had died, she'd moved to the smaller town of Pallet to get away from the sadness of her old life, and by chance she'd met the next love of her life, Maria Oak. The woman was a local professor studying the mystical creatures that inhabited the world known as pokemon, and had the two hit it off almost immediately. 

As they dated, Delia had learned that Maria had also lost her husband recently, hence her having been so keen to jump into another relationship; though she'd not been expecting to be so lucky as to find someone like Delia on her first go. 

It had also come out that Delia was no normal woman. Maria had known futanari existed, with some pokemon for example having such genders by default. But she'd never met one before. 

Delia, wishing to make a good impression, had spent a whole night making sure the researcher knew that she was just as good as a man in bed, and still woman enough for her as well. 

Their love and sex life flourished as their wealth steadily climbed as well between Maria's research and Delia's stepping into the political world. 

Their reputations grew both independently and as a couple, which let to the pair sharing a little love with others.. then a bit more.. then quite a bit a love. 

Much as they loved and cared each other mutually and as equals, both seemed to have quite aggressive, dominant urges they'd not really had a chance to explore. 

But Pallet town's population was 3/4ths women, and over the course of about a year, near enough all of them had found their way into Delia and Maria's bed. 

Far from stopping when Delia became the town's mayor, their pace only amplified, with their current fuck buddies and sex pets only aiding them gaining more, ans their positions of power letting them prevent negative fall out from those less okay with sex and love being so open and public. 

Their lives had gone up and down before they'd met each other. But together.. they'd practically ascended. 

And it was into this town, practically owned by his mothers and more open to sex than anywhere else on the planet, that Ash had been born. Loving parents, devoted servants, even loyal pokemon. He had, admittedly, not always known about the sexual side to his parents' power over the town. They wished to give him time to grow and develop before introducing him to the other side. 

The day he learned the truth was the day one of the maids first saw the bruises. Some time ago a boy by the name of Gary had started to bully Ash. 

Not wanting to worry his parents with it, he'd been trying to sort it out himself, and while he was no means weak, he also by no means experienced, and had gotten beaten up several times a week. 

The maid reported it to Ash's mothers immediately of course, and they knew immediately what needed to be done. 

That night, Delia and Maria brought Ash to one of the 'special rooms' that he'd not been allowed into up to that point. 

Inside he was hit with a smell almost completely unfamiliar to him; though he could recognize it from the scent his mothers had often given off early in the morning. 

There was a large bed, on which a woman laid. She was dark haired, tanned, stacked, and completely naked, allowing Ash to see everything. 

She was also tied to the bed, her arms and legs held out from her body and bound to the posts of the body; giving others complete access to her. Her mouth was gagged, and eyes covered by a blindfold. 

Her body seemed to tense and perk up at the sound of people opening the door and entering the room. 

Ash starred, shocked and even more so confused by the sight, as well as the sudden tightness in his pants. His body had begun developing of course, but reactions like this had never been so sudden and intense. 

“M-mom.. what is this?” He asked, speaking technically to both of them. 

“This is a sex slave Ash,” Maria said, quite bluntly; earning her a jab from her wife. 

Ash didn't have a concept of this, but his mothers would explain it to him. They started slowly of course, not wanting to overwhelm their child. But as Ash seemed to understand more, they continued to explain more. 

Sexual education had sky rocketed thanks to policies from Delia, so Ash already had a more decent comprehension of what was happening then those of similar ages in different parts of the region. 

But this.. this was an entirely new level. And to both his mothers' delight, the more he learned, the more excited his body and mind grew. 

“You'll have free access to the pets,” Delia told her son, having been waiting to for quite some time, “You may do to them as you wish, no need to ask them or apologize; though perhaps with the servants as a courtesy.” 

Ash nodded, understanding. Ash, realizing they wanted him to do so right now-and wanting to do so after seeing the woman's body like this, took out his member as he approached the bed. 

His parents gave no instruction, letting him do as he pleased to see what he would decide to do. He moved between the sex pet's legs, lining up to her pussy as he leaned over her, groping her chest roughly. 

His curiosity over such things had been waiting to be sated for awhile now, and with the opportunity to do so, Ash didn't hesitate, squeezing and pulling and smacking at the toy's tits, watching them shake and jiggle. 

His member twitched and throbbed at the sounds she made in response to his playing with her. When he finally couldn't take it anymore, he moved his hand down to keep himself and thrust in.

The lack of lubrication probably made it more painful for him than her due to her having been well trained; even if he didn't realize it at the time. 

Such roughness without lubrication would leave him sore and chaffed. But in the moment, he went all out, stuffing himself into her cunt with reckless abandoned and loving every moment. The new pleasure filled his body as he used the bound woman's body, pumping harder and faster with every few pumps, trying to force himself to the base inside of her. 

She moaned and squirmed, but didn't struggle. Ash's parents wouldn't have risked bringing him to a pet who wasn't properly broken of course. They listened with glee at Ash's moans as he hammered into the sex pet, making her body his plaything. 

He lasted longer than the average, perhaps just by virtue of good genes, though not nearly as long as Delia and Maria were certain he could. His moan of satisfaction as he unloaded a long pent up release into the pet was music to his mothers' ears. 

They'd need to train him of course. Everyone needed help and practice. But they were certain that, with it, their little boy would grow up into a sexual god. 

That had been years ago now. 

And now, in addition to his thirteen inch bitch breaker of a member, Ash's strength, stamina, and technique could match any man; even pokemon. Many had challenged him on this. 

They were all now broken.

Three women entered Ash's room, all naked. Each was gorgeous, though of differing body type. “I need to use the bathroom.” 

Ash informed the women. One dropped to her knees immediately in front of Ash, her head tilted back with her mouth open. 

Ash lined himself up and sighed in relief as he used her mouth as a urinal, filling her mouth with hot, acrid piss. She didn't even flinch, having done so before for Ash as well as his parents. 

Her mouth shut tight when Ash had finished, swallowing it easily as he wiped his tip across her cheek to dry the last few drops. Satisfied, Ash set to dressing himself for the day, then heading out of his room. 

On his way to the dining hall for breakfast, he stopped in the hallway in front of one of the maids. She was short with low cut blue hair, and even in the quite flattering maid outfits, rather tomboyish in appearance. 

Ash smirked, saying nothing before pinning her to the wall from behind. She squeaked in surprise as her dress was hiked up, her plump ass getting a rough smack before Ash's member slammed into her cunt. She groaned, gripping tight around Ash's member as his thrusts pushed her harder against the wall. 

“Th-thank you Master~” She moaned as Ash rutted into her from behind, legs wobbling from his rough pace into her. The maids were a cut above the sex slaves or pets. 

They were not allowed to turn down sex of any kind all the same, but were generally respected more. It was considered an honor among them to be chosen for such spontaneous acts of pleasure, the more aggressive the better. 

Ash grunted as he sawed into her, hilting into her before letting loose, the maid screaming out as she felt it pumping into her. 

Ash slid out of her, the maid needing to hold the wall to keep on her feet. Ash gave her ass another firm smack to watch it bounce. “Back to work.” He said before continuing to the dining hall. 

“Yes... Master... thank you... Master..” She panted in response. 

Ash arrived at the dining hall, finding his mothers already there and eating. Maria had mostly finished her breakfast and seemed more pre-occupied by groping the nearby maid; who had a steadily growing puddle beneath her making it clear how long she'd been doing so. 

Delia was more focused on her food; though beneath the table were a twin pair of maids licking and sucking on her length heatedly. Ash sat down, calling for the Milk Maid. 

Said maid, a blonde, topless woman who's GG breasts jiggled with each step, hurried over to Ash to bring him his food. 

Milk maids were given a hearty supply of Miltank milk until their own bodies began to produce very nutritious milk as well. She sat in Ash's lap, letting him bring his face to her breasts to drink from them. 

She breathed steadily as Ash drank from her, her nipples quite sensitive as a result of her task. But she did her job well, and Ash seemed to prefer her milk to the chef's food. When he'd finished, she stepped aside so Ash could speak with his parents. 

“So.. are we still in agreement?” He asked, hopeful but still nervous that they'd have changed their mind.

They'd been going back and forth for a month about whether or not Ash was ready to leave home and start his own adventurers, building his team of pokemon as well as a harem of his own. 

Delia and Maria worried their son wasn't ready for the real world; but he'd proven to them time and time again that he knew how to handle men and women, be they human or pokemon. 

And the thought of their child heading out and doing to the whole region what they'd done here in Pallet town.. Delia groaned as the thought brought her over the edge, painting the twin maids' faces. 

“We are.” The two mothers said together, smiling warmly. 

Ash smiled back, springing up to go pack his things, only stopping to kiss the milk maid to thank her for breakfast. 

He knew he wouldn't be leaving until the next morning however, so on his way back to his room, requested that Gary be brought to his room, wanting one more rut with his first sex slave before he left to start his adventurer. 

Gary entered Ash's room dressed in only high heels and stockings. He'd grown up into a remarkably girly figure. Whether that was natural or the result of his 'training' and diet, Ash wasn't sure and couldn't honestly say he cared about. 

His thigh had been marked permanently, as well as the small of his back. He was never to have both marks covered so everyone would know who he belonged to. 

Ash ordered him to bend over the bed, and gave no warning before laying into his girly ass with a wooden paddle. 

It was already well worn and marked up from previous sessions, but it just didn't feel right if he didn't redden his girly ass first. Gary winced and groaned, but didn't struggle, taking his spanking like a proper bitch. 

When his ass was red and Ash could feel the heat coming off of it from the smacks, he ordered him down onto his knees; giving yet again no warning before burying his cock in the slut boy's throat. 

He had no gag reflex anymore of course, his throat taking his master's cock easily despite it's size, allowing Ash to use it like a living onahole. 

Ash moaned happily as he fucked his toy's throat, thrusting hard down into it like he was trying to suffocate Gary. He didn't stop until he he'd given him two thick loads of cum. Gary barely had time to catch his breath before being forced down, his face against the floor as his hips were pulled up. 

Ash's member, lubricated from Gary's saliva, was forced into his well trained ass easily. It had practically been molded around Ash's cock over all this time he'd been the boy's pet. Gary granted and groaned against the floor as he took it. 

The pace he was going at would have had someone less well used and experienced screaming, but Gary's body could take it, Ash knew this well. Ash shuddered, unloading unexpectedly early into his pet as he considered having as many pets trained like this as his parents, if not more. 

He chuckled, giving Gary's greedy ass another smack before setting in for another round, just to make sure his pet remembered him~  
(

* * *

)  
The next morning, Ash was up earlier than normal, too eager to wait. 

His mothers were there to see him off of course, and while sad to see him leaving home, they were happy to have raised and trained what they were sure would become an excellent harem master and pokemon trainer. 

“You know the three rules?” Delia questioned, a last minute test to make sure their boy remembered. 

Ash nodded, “Be effective, be efficient, and be charismatic.” 

Both mothers smiled, nodding happily. They'd drilled that mantra into him. It translated roughly to 'fuck well, train them well, and know that you can't fuck everything, so be good with words as well.' 

Ash hugged his two mothers, who leaned down to turn it into a heated, sloppy three-way kiss. They held it for several minutes, almost preventing Ash leaving as they considered having a last full round. 

But Ash pulled away, giving his mothers a smile before turning around and heading off. 

There was a whole world out there for him to explore and conquer, and he was going to catch a whole hell of a lot more than pokemon.


	2. Chapter 2

Ash was barely halfway down the trail from Pallet town to Viridian city when he happened upon something interesting. 

A girl with a mess of spiky orange hair was crouched next to a busted bike, grunting and squirming as she attempted to repair whatever damage had messed it up. 

Ash's gaze moved down to her firm, tight looking ass squeezed by a tight pair of jean shorts and nice milky thighs, her position making the shorts squeeze just enough for a decent view of both. Ash simply watched her for a few moments, eyeing her like a predatory eyeing fresh meat. Had hadn't expected to find a target so quickly. 

He approached casually, “Looks like you're having some trouble, would you mind some help?” He asked, his voice so genuine and disarming. 

The girl looked up. She didn't have too much of a chest, but the yellow shirt did hug her well enough regardless. 

“I'd love some help actually, thank you.” She said with a grateful smile. 

Ash smiled back, moving over to help her repair the damaged bike. He was no mechanic, but bikes were simple enough. As they worked, he introduced himself, and the orange haired girl introduced herself as Misty. 

“That name sounds.. familiar..” Ash said, the name genuinely ringing a bell for him, though he couldn't quite place it. “Yeah.. I'm technically a gym leader.” 

She said with an awkward chuckle, “Cerulean City. I wanted to get away from it all for awhile ya know? My sisters are running things while I'm good. Slightly funny actually, it's taking all three of them just to make up for one me being gone.” 

Ash's pants were tightening with every other sentence. He was about to fuck a gym leader. A gym leader with three gym leader sisters just waiting for him. 

Ash couldn't imagine his luck. Wanting more time to learn about and make a chance to pounce, Ben continued to help; or at least make it look like he was. In truth, he was stalling, in some cases even undoing progress made without Misty noticing. 

She really didn't know much about the bike it seemed, and so had no idea how long as issue like the one she was having should have taken. Eventually, though, they did finish putting it together. 

“Maybe take a break for a bit? You look really stressed out from all of this.” Ash said with a charming smile. 

She smiled back, “Yeah.. yeah you're right.” 

She sighed, “I'm not really good with handling stress. Never have been.” 

Ash grinned, “Well, if it's not too forward, my parents taught me how to help people relax with a massage. I could give you one if you like.” 

Misty raised an eyebrow suspiciously. It was a somewhat curious offer, and she'd heard it before to try and get her into bed. But he sounded so genuine.. and he'd just spent all this time helping her out without expecting anything. 

She smiled, “Yeah.. that sounds great. Don't have to take anything off though right?” 

'Not yet~' Ash thought to himself. “Not at all, just turn around.” 

Misty nodded and turned around, Ash guiding her to sitting in his lap; though was careful to prevent her sitting directly on his ever growing stiffness; though due to its size if she even looked down, she'd likely be able to see the bulge. 

“Just lay back, close your eyes, and relax~” Ash purred as he began to knead her shoulders. 

He hadn't been lying to her, his mothers had in fact showed him how to massage. It was, they explained, an excellent disarming tactic. 

Misty closed her eyes, relaxing into the massage. It felt far better than she had been expecting. She was glad to know there were still some good people in the world. She moaned softly as she enjoyed the pleasure of the massage. The sound sent a twitch through Ash's cock. 

He was going to break this lovely bitch into a cock sleeve. He kept going with one hand, moving the other one down between her legs and to his zipper. 

He timed it for another moan from her so she didn't even hear it, and with her eyes closed, she see his bitch breaking length spring up. Ash asked her to bring her thighs together in the most soothing voice possible, using both hands on her shoulders and neck again. 

It was a weird thing to ask, sure, but she didn't bother thinking it through as she was enjoying the massage too much. She squeezed her thighs together, pausing when she felt the hot, hard appendage now pressed between them. 

She opened her eyes, but as they widened, Ash's legs moved to press against hers, keeping them squeezed around this solid dick. One hand slapped down over her mouth to prevent her saying anything as the other arm wrapped around her torso to keep both arms pinned down. 

“If you wanted to play with my cock that bad, all you had to do was ask~” 

Ash purred into her ear as he began to thrust up between her thighs, shock bleeding into confusion and anger before settling on horror as she realized fully that he was using her body to please himself, cock pumping hard between her pressed together legs. 

“So soft~” Ash praised with a smirk as his hold on her face forced her to watch his cock forcing up and down between her legs, sliding against her silky smooth skin. 

Being a swimming-a pro in fact-her legs were practically flawless. Panic setting in more now, the gym leader started to squirm and struggle against his hold to try and escape his grasp. Misty was in shape certainly, but Ash had been training for this kind of thing all his life, and easily kept a hold of her. 

In practice, her squirming did little more than make her legs feel even better around Ash's cock as her squirming pushed them against it in different and more aggressive ways, Misty effectively milking his cock without meaning to. 

Ash groaned, unloading onto the girl's sexy legs, a shudder going up her spine at the feeling of the thick, warm seed spurting over her legs. 

“Plenty more where that came from~” Ash purred into her ear. 

Misty's body was shaking by this point. She was so stirred up from this that it took her a moment to realize Ash had let her go. With her one shot to get away from him, Ash was already tearing her clothing from her body before she could move, pinning her onto her stomach with her legs forced apart. 

His hand moved back over her mouth to keep her quiet still as the other returned to molesting her breasts. Misty's panic began to well back up inside her as she realized what he was doing. No sooner had the thought occurred to her than she felt his cock slam into her very unprepared cunt. 

She screamed into his hand, the sound muffled just enough that it wouldn't carry across the wilderness and alert anyone to what was happening; even if it did, they were still closer to Pallet than Viridian, and if another citizen from Ash's hometown came, the situation would far worse before any better. 

Ash grunted and moaned as his hips pumped, forcing his bitch breaker deeper into her fit, lovely body. Her cunt gripped and squeezed around his cock, her walls feeling so good around his cock he couldn't have stopped even if he had any inclination to. 

He'd had similarly fit women before of course, but this was a gym leader. She was in a league all her own, and stuffing her felt so much better even on principle. 

It took a few solid minutes of rutting before he managed to force himself to the base, savoring the pleasure of raping the orange haired girl, knowing she'd never be as resilient or tight as this first time. 

Misty, knowing she wouldn't be able to stop him, hoped he would just finish already. While he was recovering from his release, she could reach her pokeballs. She couldn't wait to see the guy's face when he was in the jaws of her Gyarados. 

But even as they reached ten minutes of forceful pounding, he hadn't even slowed down. At the fifteen minute mark, even Misty had cum; her body too worn and too stimulated. It had been painful, but she'd gone over the edge. 

But Ash simply continued to grunt and groan as his cock reshaped her womb around its girth. Her prospects of escaping seemed to slip further and further as he continued to use her, her legs and stomach getting roughed up from the grinding against the hard ground as he took her. 

Finally, at the twenty five minute mark, right when Misty was about to give up hope, Ash finally came. 

With a sound closer to a roar than a moan he pumped far, far more cum into the girl than she'd been expecting; her vision going as white as her insides briefly as her stomach puffed up quite a bit from how much was unloaded into her. 

Her vision came back into focus, her mind fuzzy but it was just enough to reach her pokeballs when he let go of her. 

But... he didn't let go. 

Unlike what Misty understood to be normal for sex, he didn't seem tired or relaxed or even unfocused as his climax faded. He pulled out of her abused cunt and slammed with as much ruthless strength into her other, tighter, and until now virgin, hole. 

Misty screamed again as her asshole was forced apart to accommodate his cock. He was no longer holding her mouth she realized, her scream echoing around them. 

Rather than waist a hand holding her mouth shut, he re-positioned her. He lifted her hips, holding her wrists and pressing her face into the dirt below. 

She attempted to scream for help now that she was able, but with her face pressed down like it was, she couldn't get a loud enough call for help out. 

He pulled her arms like handlebars to fuck her now, grunting and moaning as he forced deeper into Misty's ass, splitting and breaking the girl. 

The searing pain radiating through Misty's body as she took Ash's length was more than she could handle, and eventually her cries of pain and attempted calls for help were mixed with choking sobs, tears running down her face and gathering beneath her in the dirt. 

Ash slammed to the base inside of her ass, only more aroused by her reaction. She'd be broken soon enough, best to enjoy reactions like this while he still could. 

His pace slowed only briefly as he held both wrists with one hand as best as he could while the other reached for his back, finding rope to tie them together with. 

This done, both hands were free. He returned them to the girl's hips, slamming into her ass harder as he could now pull her hips. 

Now, though, around forty minutes after he'd started drilling her-and about three unwanted orgasms in on her part-with her sobbing and wheezing, Ash decided to start training her. 

“You're going to be a good little pokemon,” Ash told her, “Call me Master~” 

“F-fuck you!” Misty shouted; earning a smack to the ass and a thrust into it even harder than those she'd been getting. 

“Call me Master.” He ordered more sternly. When she said nothing, she got another rough smack, after which Ash reached back into his bag and brought out a paddle, which he brought down hard onto her already reddening ass without giving her any warning. 

She screamed in pain, muffled by the ground she was pressed into. “Call. Me. Master.” 

“Y-y-yes M-Master..” Misty whimpered weakly, feeling Ash's cock throbbing inside of her ass she said the words. 

This treatment continued for the following minutes, Ash punishing Misty in increasingly painful ways when she refused or took too long to obey his commands. 

He may have once or twice intentionally preventing her being able to obey, pinching her clit painfully or picking up the pace of the rutting. He wanted to enjoy punishing her before she was too broken to even consider disobeying. 

Finally, as night started to fall, he gave the final order, “Swear to serve me, and be my personal cock sleeve for the rest of your life.” 

Ash was nearly surprised how quickly she complied, agreeing to do anything and everything he asked of her for the rest of her life. The painful stimulation had broken her some time ago, Ash hardly noticing as he'd filled her ass with more cum. 

He smiled, switching back to her pussy, figuring he'd keep her there until morning. A perfectly little cocksock for the night.


	3. Chapter 3

It had been quite the walk to Cerulean, though this had at least gotten Ash time to catch some pokemon, and enjoy Misty further as she told him about her three sisters. 

She evidently didn't believe for a moment they were actually doing a good job acting as gym leader for Cerulean, but after so long of pulling all the slack and still getting shit from all three of them for it, she hadn't been capable of caring enough to stay. 

The story amused Ash, though not as much as the thought of how much fun they'd have when they got there. 

“Violet, Lily, Daisy,” Misty greeted as they approached together. 

Ash smiled at them as they did. It was his usual well trained charming smile, hiding the intentions behind it. 

The three sisters were dressed in dress like swim suits that hugged their figure beautifully and showed quite a lot of their long, smooth legs. Ash could feel himself stirring as he looked over their bodies, but managed to control himself, at least for the time being. 

“Didn't expect Misty to be coming back with a boyfriend~” Daisy teased with a giggle. 

She had, perhaps, been expecting Misty to deny that they were together and be embarrassed, as all three went silent and wide eyed when Misty simply shrugged and said, “Never know what you're gonna find out there~” 

After that, their congratulations and questions, even their tones of voice became much more genuine and serious as they invited the pair to the gym's backroom to hang out for some time. 

Grinning at this, both accepted, following them back as the sisters brought out snacks and drinks for everyone to celebrate Misty's return and her new boy toy. Both giggled at this, knowing which of them was the toy in their relationship; if it could even really be called that. 

They sat and talked about whatever came to mind. Ash and Misty thankfully didn't really have to make up a story for how they'd met, just omit some details. The sisters found it to be the cutest thing they'd heard in ages. 

All three, being older sisters and Ash being rather handsome, teasingly flirted with Ash as they talked. All three were surprised to find Misty not asking them to stop nor even seem upset by it, even when Ash flirted back with them. 

She'd always been rather defensive around the three of them. Boy must have changed her more than they'd thought. They couldn't have guessed how right they were. 

They asked Misty if she was alright a few times. The way she sat there.. eyes half glazed over.. she looked like someone who'd been hit by a Hypno's hypnosis. She responded just as natural as ever when addressed, but when not spoken to, she just seemed to turn inert. 

The sisters were a bit too air headed to question it as much as they should have though, nor did they notice Misty slipping something into their drinks as they spoke. 

By the time they noticed anything wrong, they were waking back up after having been out cold for quite some time. 

All three were naked, their arms and legs bound with rope, their mouths gagged, and their bodies positioned so they could watch Ash as he plowed into Misty's ass. 

Misty took it like the cheapest whore on earth, not resisting in the slightest nor seeming to care when she saw that her three older sisters were watching her be drilled like an oil field. 

The sisters had been out for quite some time, so Ash was nearly finished with Misty. All three sisters began to squirm and struggle as blind panic set in, only Violet the least bit aroused by the scene before her. 

Ash could see it, could tell from the way she moved as she struggled against the ropes; especially when compared to the other two sisters. He grunted, unloading into Misty with a sigh of relief. He slid out of her, the sister's eyes widening as they saw the full length of the boy's rod. 

He moved over to Violet, pinning her beneath him and slamming into her ass without any further warning. He was rough at first, violently plowing into Violet to break down her resistance. 

After several minutes of this, when he could tell her body was vulnerable, he reigned it in, hips moving slower, more sensually. His hips rolled as he fucked her, finding her weak spots and exploiting them, slowly chipping away at her more and more with the techniques his mothers had taught him to use. 

After another ten minutes of this, and the third orgasm from Violet, he removed her ballgag and was delighted to hear her begging him to keep her like she now knew he was keeping Misty. 

He smiled, rolling her over and kissing her as he unloaded into her ass the same way he has Misty, giving her forehead a kiss before sliding out and moving to Daisy after he'd finished untying Violet. 

The two moved to Daisy together. 

“She's got a really sensitive chest,” Misty informed her master, “Used to hear her talking about things she let guys do to it all the time when she thought I'd gone to sleep. Really was a whore before she had to take over the gym.” 

Despite not a word of it being untrue, Daisy found herself feeling both shocked at Misty for saying this, and flustered beyond belief. She'd had the sketchiest past of the three of them sure but that had been the past, this was now. 

But now, it seemed, involved being raped, so perhaps it made no odds.

After watching Misty and Violet get violated, she wouldn't have been caught off guard by Ash moving to fuck her next. 

Perhaps that was why he had Misty pounce on her first, groping and sucking and pulling at Daisy's chest with her teeth. The thought of her little sister doing this was enough to boil Daisy's brain, but the actual sensation accompanying it was utterly frying it. 

By the time Ash called Misty off, Daisy's whole body was shaking and on the edge of a very uncomfortable, unwanted orgasm. Ash snickered at her expression, wondering if he should have let Misty make her cum and use the shame to break her even faster. But.. nah, more fun to do it the hard way. 

Misty moved to Lily at Ash's orders, tracing her fingers along her body before burying her fingers knuckle deep into her cunt, making her third sister groan against her gag as Ash pounced Daisy, pinning her on her back. 

He lift her bound legs up and slammed into her cunt. He'd known that she'd be tight from how in shape she was, but the position her legs were in make her body squeeze even tighter around her. 

She cried against the gag, continuing to squirm; but this did next to nothing save for make her feel even better around Ash's cock as her hips moved, making him give up on going slow and starting pounding into her like he intended to leave a dent in her womb. It certainly felt like he was going to, her body writhing as she took his cock helplessly. 

Her forced her legs forward towards her head. She was flexible, so it didn't hurt nearly as much as it would for most, but was by no means comfortable. 

With her body bent over like this Ash could reach her breasts and continuing to torment them like Misty had, groping, pinching and pulling on her nipples, smacking, then pushing even more to lean down and suck as he sawed into her tight cunt, forcing himself balls deep with each thrust to make her take all of him. 

Daisy screamed into her gag, but gradually grew quieter and quieter until her was reduced to low groans and whimpers against her gag, cumming violently by forced. After she failed to hold in a fourth, her eyes started to roll back, her body simply giving up and leaving her mind to its own devices. 

That losing battle lasted all of ten seconds, her body going utterly limp, a fuck doll for another five minutes it took Ash to cum, flooding her sore body with seed. 

He slid out of her happily, stroking out the last first spurts onto the girl's tits. He wasn't sure if she was conscious enough to feel it, but it felt like the right thing to do. 

His hungry, greedy eyes turned next to Lily. Misty had her sister so riled up her hips were bucking against her fingers. Whether she was doing so intentionally or if her body had already given into pleasure Ash wasn't sure, not did he especially care. She'd be his soon regardless. 

Before he could start, though, he heard noise outside the room. Opening the door to investigate, he saw that a boy had entered the gym, presumably to challenge its gym leader; or gym leaders as the case may. 

Ash's annoyance slowly gave way to excitement as he looked the boy over. He was a cutie, and it was rare he had pets walk right into his clutches. 

This was going to be fun~


	4. Chapter 4

Misty stepped out of the room and approached the boy who had entered the gym. Ash had instructed her to act as a worker and get the boy to 'join them in the back'. She was dressed, though was wearing no underwear of any kind beneath. 

Looking over, Misty maintained a perfectly straight face, pretending she didn't notice the boy noticing her hips, the way her hips swayed as she walked. 

“Welcome to Cerulean city gym. Unfortunately the Sensational Sisters are out for the moment. May I get your name?” She asked as formally as she could manage. 

“Richie,” he introduced, “Sorry I didn't know, it looked like the place was opened. Was really hoping to challenge them today..” 

Misty gave a smile, “Well.. I don't usually do this, but..” she pretended to look around before she spoke, like she were doing something she shouldn't; which she arguably was anyway, “I could let you hang out here for awhile, I can bring you a drink while you wait in another room. You'll be the first to challenge the sisters when they return.” 

Richie smiled, blushing somewhat at the pretty girl wanting to go out of her way to help him so much. “That'd be great, thank you.” 

Misty nodded, taking his hand to lead him to another room, which only deepened his blush. As promised, he made Richie a drink; spiking it just like she had with her sisters. 

He didn't notice it, and when he started to feel it hitting and grow suspicious, she grabbed his head and pulled him into a deep, sloppy kiss. 

Already loose from the spiked drink, Richie's suspicion was buried by desire as he held onto Misty. She let him, making out with the boy until he passed out fully. 

It was some time later when he woke in the actual back room to the gym. Just like the sensational sister's before him, he woke naked, bounded, gagged, and with a view of Ash fucking someone; in this case Lily. 

He had discovered by trial and error that Lily was fond of having her ass abused, and had beaten it bright red as he drilled her pussy. She was incoherent, moans being all that escaped her mouth. Said mouth was being forced against Misty's cunt. 

She'd learned already she'd be punished if she didn't her out like she'd been ordered, so simply gave up on speaking and buried her tongue as deep inside her sister as she could, eating her as best she could with so little experience and while being rutted like a submissive bitch. Richie stared at this, wide-eyed. 

It was perhaps the hottest thing he'd ever seen in person, and was stiff as a board in seconds. Were he not also bound and gagged with no idea how he'd ended up that way, he might have been considering joining them. 

Daisy and Violet approached the boy. They'd been given time to rest since being broken, and now had their orders to keep Richie ready. 

Certain by this point it had to be a dream, he simply went with it as two of the Sensational Sisters kissed him, pressed their breasts against him, stroked and sucked him; though never letting him cum. 

Soon Daisy began riding him, bouncing on his needy, desperate member. Nearby, Ash was finishing up with Daisy, bloating her with his release as he gave her ass one final strike. 

He'd practically branded her ass with his hand print by this point, and chuckled at the thought as he pulled out of her, watching her lay there, broken and helpless for a moment before turning to Richie. Daisy had moved Richie's bound body, laying on her back with her legs locked around him to keep him fucking her. 

Grinning, Ash moved behind the boy, admiring his cute ass for a moment. Richie was so focused on the beautiful woman he was fucking, he didn't even notice Ash until he felt his monster of a cock ramming into his extremely unprepared asshole.

He screamed in pain as his walls were stretched apart like Ash was trying to break him in to, silenced by Daisy pulling him into a kiss as the stimulation forced the boy to cum into her. After that, she pulled away, leaving him to Ash. 

Ash held him up, as it made for a better angle to pound into his formerly virgin ass. 

“So good~” He moaned into the boy's ear, “No use struggling cutie, you're all mine now~” 

Richie wanted to panic, to struggle, to break free or at least cry out for help, but his brain was misfiring. The pleasure from cumming with Daisy and the intense pain of having his ass so brutally initiated was making it impossible for him to think or really respond outside of cries and screams as he felt Ash's cock push deeper into his body than he had thought possible for a human's cock to reach, stretching it out so much he wasn't certain he'd survive the fun. 

Ash was on cloud nine. His hands moved along Richie's body, teasing his nipples and cock, though more dominantly than Richie ever expected to feel. 

Ash was going to enjoy using Richie, more than he had enjoyed the sisters perhaps. It had been nearly a week since he'd gotten to fuck Gary, longer still since he'd had a nice cute boy's first time all to himself. He'd missed that feeling more than he'd realized until this moment. 

Unlike the sisters, who he was content to stop after they gave in, he doubted he would be able to stop with Richie until he had drained himself. The boy would be far passed broken by then, and it would take hours. But it wasn't like Richie had anywhere to be now that he belonged to Ash of course. 

Richie's cries were soon reduced to weak sobs, his screams into groans, the last loud noise when he felt Ash cumming for the first time, his entire body growing tense at the burning sensation spreading throughout his body from the thick cream pumped into his body. 

“Better get used to it honey~” Ash purred, biting Richie's shoulder as he continued to saw into Richie. He'd be taking plenty more even just tonight.

Only a week and some change in and Ash already had five pets. His mothers would be proud of him, he knew it. And he was barely started~


	5. Chapter 5

After the fun in Cerulean, it was time to move on. 

There was still more to see and much more to do of course. Ash wasn't so proud that he couldn't admit he may have gotten a little caught up in the fun. After a few days though, the universe seemed to give Ash a little nudge in the right direction. 

Ash and his harem were having their usual fun when the light suddenly cut out. All the power in fact. This lead to more than a little shock and confusion, but after some looking around, the culprit became clear.

A Pikachu had buried its way into the gym and started nibbling on the wires; attracted to the electricity no doubt. Ash found them before anyone else and, acting before he could really think, grabbed a pokeball and threw it at the mouse pokemon. 

They struggled, but were captured nonetheless. Thankfully not much real damage had been done to the wires and it was sorted within a few minutes, but now there was the matter of the new pokemon on the team. 

Ash figured there was no sense beating around the bush. His pokemon needed to trust and know who he was after all, as well as know that he was in charge. There was the slight issue of the electricity.. but thankfully, there was a solution. 

Pikachu produced and released it from the sacs in their cheeks, and for this reason, insulated caps had been developed to help trainers with violent Pikachu, or just Pikachu who could not yet control their power. 

With a little speed, and rubber gloves, the caps were placed on the Pikachu, who seemed more confused than upset for the moment. 

“I captured you,” Ash explained, “You're going to join my team.” 

The Pikachu looked not exactly surprised. They knew what had happened but it only seemed to settle in now. They seemed more resigned than angry. 

It would at least mean regular fun and protection, training to get stronger. As the Pikachu thought this though, it realized that the human was undressing. 

In fact, looking around, most of the humans in the room were naked. The Pikachu was remarkably confused by this, and began to grow nervous as Ash sat back and lifted the Pikachu up. Reflexively he tried to shock Ash, the electricity halted by the caps. 

Below him Misty engulfed Ash's member, lubricating it with her mouth and throat, “Now listen,” Ash said, his voice more gentle and far more genuine than usual, “My pokemon will be my team members. You'll learn to fight, you'll be fed, and you'll even get plenty of fun along the way. But it's important you remember who's in charge as well.” 

The Pikachu whimpered nervously at this, but couldn't do much. Physically it couldn't wriggle out of the human's grasp, and with its cheeks capped he couldn't do much of anything. He heard a pop as the human below pulled off Ash's cock. 

The Pikachu whimpered as he felt the tip of it press against his hole. The difference in size was.. unnerving. But there was nothing he could do. 

He wasn't dumb enough to risk making this human angry, and so took a breath to relax his body and let it happen. Ash smiled, encouraging the Pikachu with a small kiss to the forehead. 

Rather than slam the Pikachu down onto his rod, he rather lowered them down gently, letting them gradually get used to the size as it pushed inside, stretching the mouse pokemon's tight, formerly virgin hole. It squeaked and cried out from the sensation, but didn't struggle. 

Misty and indeed her sisters were slightly awed at how comparatively gentle their master was treating this pokemon. 

Comparatively being the operative word, as the pokemon's body started to bulge from the size of the member pushing into it before Ash even had him a third of the way down. The Pikachu's teeth grit as it realized this and prepared for the worst. Worse did come, but not the worst. 

Ash forced the Pikachu down to the halfway point, his thick, solid rod twitching inside the soft, tight pokemon. His instincts wanted to just go all out and rut the pokemon silly like a fuck toy, but no. This wasn't some slut or worthless onahole. This was a pokemon, a partner. 

He was to establish dominance not break them, another of his mothers' lessons. Rather than force the pokemon to the base, Ash began to move the pokemon back up, resolved to only use half, as that was more than he needed to make his point clear. 

The Pikachu groaned and squeaked as Ash gradually picked up the pace, fucking the electric type. It hurt yes, but wasn't near as bad as the Pikachu had been expecting. In fact, after a few minutes of this, with his prostate repeatedly hit, pleasure even started to set it. 

It was even enough for the Pikachu to cum after a few minutes more, its smaller member spurting over the pokemon's yellow fur as Ash practically pumped him up and down his much larger rod. Finally Ash felt his own climax brewing. 

He pulled the Pikachu from his rod, placing him down in front of himself, instructing the Pikachu to finish the job. 

Obediently, the Pikachu gripped Ash's shaft with his small paws, licking at the tip as he stroked it with both. After a few moments of this, Ash erupted, utterly painting the Pikachu, and officially marking him as Ash's. 

He sighed in relief at the feeling, “Very good~” He praised, giving the Pikachu a smile that made the Pikachu smile back, albeit weakly. 

Ash had Misty get the pokemon washed up, the caps removed from his cheeks now that he was sure the pokemon knew who was in charge. Sure enough, no escape attempt, no electrical attacks. Pikachu knew what was what now, and was rewarded for it, Ash instructing Misty to also handle any desires for release the pokemon wanted. 

Doing such things with a pokemon was a new experience for her, but she couldn't disobey her master, and did so happily. 

The orgy that the Pikachu's arrival had interrupted carried on long into the night. And come morning, plans were being made to leave. 

Ash remembered now that he needed to keep going, needed to start capturing pokemon as well as harem members. Only Misty and Richie would be coming with him though. 

The Sensational Sisters suddenly stopping their shows, along with there no longer being gym leaders, would be a bit much. He did instruct them that a portion of the funds they made were to be sent to him, assuring their master would be well funded. 

He also ordered they take their gym leader work seriously. It wasn't something they were used to, but for their master, anything. The next two weeks were equal parts blur and adventure. Not far from town he'd found a Caterpie. 

He captured it immediately, knowing they'd need to be evolved before they were dominated; though weaker pokemon tended to be more obedient innately. 

For that same reason, Ash pounced on the Charmander he saw immediately, knowing even the remotest amount of weakness would instill disobedience in that kind of pokemon. The fire pokemon hadn't even seen Ash approaching and could do nothing but cry out as it was pinned against a rock, the much taller human slamming his cock into their body. 

With its claws held over its head with one hand, face to the rock, and tail held away from Ash's body with the other hand, the Charmander was helpless as Ash rammed into the fire type. He was a bit more aggressive with the Charmander than he'd been with the Pikachu, partially out of necessity, this pokemon's species was all about shows of dominance, partially out of how amazing it felt. 

If he'd known how good rutting a fire type would be he'd have started with one. The Charmander was perfectly obedient after that, more so still after he allowed the Charmander to pounce on Richie and make use of the boy's ass. 

He found the Bulbasaur next, one of the only two pokemon he actually battled but my no means a challenge. Having been training his pokemon, the Charmander's fire power was strong enough to practically one shot the grass pokemon. A hit to the pokemon's ego, which was a shame. 

The whole reason Ash had gone for it is that he'd seen how strong the pokemon was already, even defeating other, albeit weaker than Ash's Charmander, fire pokemon. 

The Bulbasaur was especially aggressive in trying to escape Ash's dominant initiation, potentially more so than the Charmander, but in the end accepted it just like all the others. 

By this point, the training had gotten the little Caterpie all the way up to a Butterfree. Still fragile, more so even than the Pikachu, Ash had to be the gentlest with them; though having evolved thanks to Ash's training, grown attached to him, and watched the other pokemon get the treatment, he didn't really need it to be especially rough. 

Hell, the Butterfree almost seemed to be looking forward to the treatment. The most difficult to deal with had been the Tauros. The strong, aggressive pokemon easily broke out of pokeballs and charged Ash repeatedly. 

Finally, through a combination of Butterfree's psychic attacks, Pikachu paralyzing it, and Bulbasaur binding it with vines, he managed to capture the wild beast of a pokemon. 

Dominating them was likewise difficult. If Ash hadn't been trained to handle such things the attempt alone could have left him permanently damaged if not outright killed. It took hours, but like all the rest, he managed. The most fun for Ash personally had been the Nidoran. 

He was male, and when he found them, they were indulging themselves with the company of a female. 

The two were too preoccupied to notice Ash approaching. With a guard on to protect his body from the spines, he pounced, practically trapping them beneath him as he slammed into the male Nidoran, making them shriek. 

The force of Ash's thrusts was added to the Nidoran's, causing them to fuck the female silly beneath them. Ash hoped this would not only help establish his dominance to the male, but also show him the pleasures of being with Ash's team. 

And indeed it did, the Nidoran, while shellshocked, more than willing to join Ash when all was said and done. 

Now having a full team of six, Ash set to seriously training them all, getting them all ready for the conquest the same way he had. He told Misty and Richie to do the same, and soon the group was strong enough for Ash's liking. 

At the end of the two weeks Ash found himself in Celadon, intending to challenge Erika, the local gym leader. He'd had the idea that he could try and claim her for himself of course, she was rather attractive so of course it would at least be on the table. 

He hadn't been certain though until he met her. 

“Well, it seems another useless boy wants to challenge me.” Erika said with a roll of her eyes, her peanut gallery of assorted female trainers all chittering and snickering like trained parrots. 

Ash didn't have a problem with her only choosing to hire female trainers, that was her right and her choice. He didn't mind her being 'high class', he himself came from an extremely wealthy family. But the grass gym leader just did not seem capable of not being an utter high and mighty bitch for even two-tenths of a second. 

Every other sentence seemed to contain some veiled or even just outright stated insult. His training, his appearance, his family, all seeming to tie back to the fact that he was male. 

Any other male received the same treatment while female trainers were treated sweet as could be. 

One day, he finally decided that enough was enough. Ash waited until nightfall, when the gym trainers would all leave. Erika herself slept in a backroom in the gym, and would be alone save for her pokemon. 

As she was a gym leader, that generally wasn't as issue, as they could take care of themselves. But she'd not been properly acquainted with Ash, not yet. But she would be. 

With his other pokemon standing guard, Ash and his Bulbasaur snuck into the gym carefully. 

While his mothers' training had resulted in sexual skills and flashy combat talents, stealth and agility were also trained into him, as they'd been just as needed. He'd complained at the time of course, but now was grateful for them. 

He crept into Erika's room, and was on the sleeping gym leader in moments. She woke quickly, but not quickly enough. Her sleepwear had already been tossed aside and her limbs tied. Her panicked struggle became even more frantic when she felt Ash forcefully tear her underwear from her body. 

She opened her mouth to scream, only for the noise to be muffled by the very same underwear; Ash shoving them into her mouth as an impromptu gag. He gave her chest a rough smack before slamming into her tight cunt. She let out another scream that was muffled by her own panties as Ash let loose. 

Much as he loved his pets, it had been more than two weeks since he'd last broken someone, and the urge had only grown more and more with each passing day. 

Combining that with his desire to teach the stuck up gym leader a lesson fueled his already lustful heart. His hips pumped like a machine, forcing his entire length to the base repeatedly despite the resistance of her tight, unprepared body. She writhed in pain and forced pleasure as she was drilled into oblivion, useless against the restraints. 

They were Ash's best, a bit improvised, but he doubted she had any kind of experience trying to escape such a thing. As much fear and confusion was flowing through her as the waves of sensation crashed into her, it wasn't until she was what Ash's Bulbasaur was doing that she really started to break. 

Nearby, her beloved Gloom was being violated just as aggressively as herself. The Bulbasaur's vines bound the fellow plant pokemon as it pounded into her without a speck of mercy. 

Being just as poisonous in nature as the Gloom, the dust it let off did nothing to stop the Bulbasaur as its cock hammered into her. 

Tears rolled down the gym leader's face as she realized the extent of the situation. 

With the last of her resolve, she redoubled her efforts to escape. It was useless however, and the attempt earned her nothing but several harsh smacks across her breasts and face as Ash used her body like a sex doll he wanted to pop. 

Slowly, the futility of the situation set into her, but even as both she and her Gloom gave in, neither Ash or his Bulbasaur slowed down. Their punishment would last hours. 

After their cunts had been so pumped full of cum they couldn't take anymore, the two switched their their preys' asses, pressing their helpless bodies against one another as they were fucked senselessly. 

Ash was quite certain both of them broke much earlier than when they stopped pounding into them, but he needed to make a statement. 

He needed to fuck that high and mighty attitude out of her. He untied her afterwards, knowing that even if she weren't broken, she'd not be physically able to run. 

He pulled her up by her hair, bringing his member to her lips, “Show me you're a good pet, and you don't have to be punished anymore.” 

He didn't bother making sure she understood, a small part of him wanting her to fail. He pushed his member into her mouth and sighed as he released his built up urine into her mouth. 

The gym leader tensed at the taste and realization of what was being let into her mouth, but she didn't even consider disobeying, swallowing it all without thought. She gagged of course, but she obeyed, her eyes glazed over and her mind broken. 

Ash smiled, “Mission complete~”


	6. Chapter 6

Erika's gym had more gym trainers than most others in the region, perhaps more than any other; all of whom were female do to Erika's previous gender biases.

It was essentially a buffet for Ash, hence him spending even more time in Celadon city than he had in Cerulean, breaking all of the ladies to his whim and training their skills in the bed one after the other. Once all of them were well broken and even better trained, Ash had Erika open the gym back up. This time though, not as a gym. 

Her gym was now a brothel, herself and the other ladies its staff. The population of Celadon had lusted after the gym trainers and Erika for years, men and women alike, so the market was ready made for them; another revenue stream for Ash. 

He didn't technically need the money, but it felt better to have earned the resource than simply be given it by his parents. 

Not keen on another long trek, and having seen a picture of the town's gym leader, Ash set his sights on Saffron city; more so its gym leader. And this may well be the first thing Ash had done that could be considered a definitive mistake. 

Mistakes two and three being not doing any research on the woman followed by waltzing into her gym like he owned the place. Richie and Misty, equally uninformed, simply followed along, eager to see their master claim yet another sexy woman. 

Ash realized not only that this had been a mistake, but also the scale of it mere seconds after he entered. 

All three of them were lifted off their feet and slammed into the nearest wall, pinned in place as the dark haired woman stepped into view. 

Ash opened his mouth to speak; only to find he couldn't. Her psychic hold on him was too intense. Ash had never seen a true psychic before, and had never developed such a power himself. 

“No need to speak,” Sabrina told him, “I can read your true thoughts.” 

Feeling fear for potentially the first time in his life, Ash slightly hoped she was bluffing; as if she didn't like what she saw, she could crush him like a soda can without moving a muscle. Ash had never been at the will of someone else, not since he'd started his training as a kid. It was terrifying. And yet with that fear came a sense of.. connection. 

The will of this woman was astounding, and her being inside his head only made him feel closer to her, a kind of connection he'd never felt before. 

Ash watched as her straight face shifted slightly to surprise, redness growing on as her legs moved together. 

Ash felt his body move, pulled away from the wall and towards the psychic gym leader until he was floating directly in front of her. 

His fear, such a foreign emotion to him to begin with, only spiked as this happened, worried what was about to happen to himself and his pets. He relaxed somewhat when she pulled him in, her lips pressing to his own, but he could tell this woman hadn't simply conceded to him. 

This was not a submissive kiss. Sabrina dominated Ash with it, made it clear who was in control. He'd never felt such power from someone he'd been attempting to tame, and wanted more of it the moment she pulled away. 

“You believe you can conquer me do you?” The woman questioned, “Come and try it boy.” 

Ash was dropped to the ground, stumbling a bit as he found himself shaking for the first time he could remember. 

Before he could remove anything, Sabrina's telekinesis had stripped him naked, making him blush; something else he couldn't remember doing in quite some time. 

Sabrina herself was now naked as well as the two of them moved towards the gym's field, smooth, plump body on full display as they walked. As they stood before one another, the passion of this woman making Ash even harder than her gorgeous ass or DD breasts ever had, he heard moaning and cries. 

Looking away from Sabrina, he saw that the gym assistants, trainers and scientists who studied ESP, were all either naked or partially stripped, toys controlled by Sabrina fucking all of them simultaneously. 

Ash was astonished. This woman was not only passionate and powerful, she was truly in control of this gym. She was not offended by his desires of sex, this was clear. 

This nympho maniac was, if anything, interested by the challenge Ash presented her. Ash wondered if he even was a challenge, and was unsure why this thought sent a shiver up his spine. 

But she had offered the challenge, and like hell was he going to turn it down. He stepped forward, almost instantly forced to the ground by Sabrina's will, pinned on his back. 

For a second Ash wondered if this woman, the first other than his parents he'd seen as an equal, had already deemed him not worth her time. 

This thought left him as he watched her step over him, taking a seat on his face for him to eat her out. Ash buried his tongue inside Sabrina, his member throbbing at the sound of her moans. Sabrina had seen women break in the passed, had broken many, men as well. 

She'd even seen Ash do so as she scanned his memory. They were weak Sabrina thought, and still thought so now. But she was nonetheless surprised by Ash's skill; the speed with which he found her weak spots, her g-spot as well, the skill and power with which he assaulted them. 

Ash felt her psychic grip on him weaken as he ate her out, the surprise of the rush of pleasure taking her focus off of him. Resisting the urge to lose himself in the taste and feel of her, Ash pushed forward, holding Sabrina's hips to continue eating her out as he sat up to change their position. 

One hand moved to her round, lovely ass, fingers pushing in with as much skill and even more strength than his tongue. As fascinated as he was by this woman, he was still going to try and make her his. It was in his nature to break beautiful women of course, one being powerful didn't change that. But he knew it wouldn't be easy. 

No sooner had he made Sabrina cum did she return the favor in a way he'd never felt before. As she came, with her pleasured cry came a surge of psychic energy, pleasure washing through everyone in the room. Richie and Misty screamed as they came, writhing against the wall. Ash came with them, shaking at the feeling. 

But her power only caused his own fire to burn hotter. 

“You'll be a trophy,” He growled, pushing down to pin her on her back as he moved over her, member lining up to her slit, “A trophy of my true dominance.” 

He'd never said such things without confidence he could follow through before, and not wanting this to be the first time, he kept going. 

He rammed into her tight cunt, shaking at how perfect she felt around his member, her muscles gripping around his cock and seeming to swallow him in. 

Her body wasn't just tensing up from the stimulation of someone cumming or breaking mentally, she was just in control as he was. As he hammered into her, forcing his length deeper into her hot, lovely body, he got confirmation of this as her psychic power washed over his own again. 

The pleasure was the greatest he could recall, flowing through his body like warmth but just as intense as the pleasure he was getting from pumping into her. His hands moved along the gym leader's body, massaging it to make her moans grow louder as he sawed into her. 

Sabrina had to admit, she'd never been fucked like this. She had called him a boy before, a statement she now regretted. This was a man she had challenged. Ash was equally stunned by this woman. He'd broken gym leaders before, but this was something different. 

He doubted she would break at all. She was a true woman, one that would take all his skill and strength just to satisfy properly. Another wave of psychic pleasure washed through the room as Sabrina came, making sure all in the room followed her, even Ash himself. The two stared into each others eyes as they panted from the intense release. 

They moved in at the same time, kissing heatedly, their tongues fighting against one another. They truly were equals, both knew it. 

Misty, Richie, and all of Sabrina's workers were called forward; released from the hold Sabrina had on them. Both groups were used to seemingly endless fucking sessions, but the aura of pure heat and passion coming from their masters... broken as they were it frightened even them. 

And for good reason. 

Not a one of them was given a break as the two fucked throughout the night, always having one or several of the others to focus their more dominant desires onto as Ash and Sabrina not so much fucked as.. made love. Most passed out long before the two were done with each other. 

When Ash woke late the following afternoon, he was surprised to not only find Sabrina awake, but already riding him, ass taking Ash's cock wonderfully while all the others were out cold, cum still leaking from their holes or drying on their bodies. The woman truly was remarkable. 

“Will you become my partner?” Ash questioned, “Travel with me, build our harem together?” 

He could never break a woman like this, not with a thousand tries. But he knew he needed her. If not a pet, than an his equal, his wife. Sabrina smiled as she looked into the eyes of the first person she'd ever even consider such a thing with. 

She leaned in to kiss her mate, sealing the deal without need of words as her ass continued to milk him. Ash didn't know how long he'd stay in Saffron. He doubted he'd be able to pull himself off/out of Sabrina for at least a week. 

When they left, though, they'd make this gym a brothel as well. Sabrina had read the thoughts from Ash's mind of what he'd done to Erika's gym, and already had her non-fuck pet staff working on preparing for it. 

Ash had not expected this result, never would have. But overall, he couldn't help but consider it a complete success.


	7. Chapter 7

Ash and Sabrina sat together happily, watching Richie and Misty rutting. The pets were allowed to play among themselves. Misty was more than happy to fuck anyone on her master's orders of course, and Richie only ever got to be on that end of a fuck when it was with others. 

Richie hammered into Misty, who was laying on her back with her hips up, taking it easily. After taking Ash's for so long she could easily handle Richie's member no matter how rough he went with her. 

Sabrina had one hand in the air, controlling two dildos sized after Ash's member, forcing them to thrust roughly into Richie and Misty's asses as they fucked each other. Her other hand was working along Ash's member as he enjoyed the show with her, Ash's fingers returning the favor between Sabrina's legs. It was amazing to have Sabrina with him. Someone so powerful and dominant, someone he could truly admire. 

The feeling was mutual, something Sabrina could read in his mind of course, which had been what ultimately made her decide to travel with him, the first male, hell the first person, she'd found who was like her in this way. As they enjoyed the show, their pokemon were training against one another nearby. 

Most had horrible trouble against Sabrina's psychic types.. and Ash's were no different, though they fared far, far better than any of their kind should have managed, and with their help training, they'd only get stronger. As they trained though, Sabrina sensed something from one of them, and turned to her mate. 

“Your Charmander is close to evolving,” She informed him, “He's aware of it, and excited for how much stronger they'll become.” 

Ash smiled, leaning in to give her a kiss. Sabrina's senses were yet another perk of such a powerful lover. She loved using it on Ash the most, finding peeking into his mind, his inner thoughts, somewhat intoxicating; so perverse and delectable~ 

But she also kept her eye on those around them just to be safe. After he pulled away from the kiss, Ash stood up and approached the training pokemon. 

He wanted his team to be powerful of course, and didn't consider them to be as submissive and broken as his pets; as if they were it would all but certainly weaken them. But the Charmander was a special case. 

His species was so innately aggressive and rebellious, and with the potentially to act out even more with each evolution if precautions weren't taken. The Charmander panted genuinely, enjoying his ever growing strength. 

He couldn't wait to evolve.. and didn't notice Ash approaching from behind until the trainer pinned him to the ground. 

“Thinking of evolving without letting me know were you~?” He questioned as he held the pokemon down. 

Rebellious though he was, the Charmander was still frightened of Ash being angry with him. Ash smirked down at the pokemon, saying nothing further before thrusting forward, burying his member, still stiff from before, deep into the fire type's ass. 

The Charmander cried out as his walls were stretched out by his trainer's cock. While he'd taken it before of course, the pokemon were not involved near as often as the pets, and so the Charmander was not nearly as used to it, the sensation just as intense as the first time. 

He didn't dare burn Ash with his tail, not even by accident, diligently keeping his tail away as Ash hammered into him, moaning at the warmth of the reptilian pokemon's body. He really did need to find more fire types, they felt so wonderful inside~ 

After a few moments of rutting him against the ground, Ash moved back, lifting up back to his feet with the Charmander on his cock, now being bounced on his trainer's cock by the force of his thrusts. As he slammed into the fire type, Ash waved over his Butterfree. 

She knew what to do without needing to be told, fluttering over and down to the Charmander's stiff member. 

She gripped it with her small hands and set to sucking the larger pokemon off. She may have been small and relatively frail, but Ash and the others had learned that she was a marvelous cock sucker, and seemed to actively enjoy doing it. Perhaps because other forms of sex were a bit more damaging to her. 

The Charmander cried out harder now, member erupting almost immediately into the bug type's mouth as he felt intense, overwhelming stimulation. Ash didn't stop, nor did the Butterfree, the sensation's made only more intense by how sensitive the fire type post climax. His cries became even more erratic as his eyes started to roll back. 

If anything, Ash picked up the pace, cock slamming to the base inside his pokemon with each thrust, pounding against his prostate aggressively. As he essentially melted from the pleasure, the fire type's body began to glow a bright white. Ash grunted, going even faster now as he felt the Charmander grow around and against him. 

The Butterfree didn't slow either, swallowing down a second release she milked out of him as his member began to grow larger. The light faded slowly, Ash grunting as he let loose, unloading into the Charmander, now Charmeleon. 

Ash slid out of the fire type, allowing him to collapse onto his back on the ground, panting heavily with glazed eyes. Ash moved over to the pokemon's head, bringing his cock to his lips and thrusting inside. 

Any other Charmeleon would have been fighting this, perhaps biting or blasting fire. But Ash had successfully broken the fire type; complete obedience. 

He simply accepted it, sucking his trainer's member as the Butterfree fluttered down and bringing her face to the Charmeleon's dripping hole to clean Ash's seed from it. 

It'd be odd to have a Charmeleon, more so a Charizard, that didn't have passion with its movements, but better that than one that defied him of course. 

And as he moved from being sucked to skull fucking the Chameleon, using the horn-like growth on the back of his head like handles, a thought became clear in his mind. Some time back he'd sent his Tauros to his mothers as something of a gift, freeing up a space on his team. 

Feeling the pleasure of this powerful, aggressive pokemon broken by his cock, Ash knew immediately what he wanted on his team. 

Ash planned to find and break and legendary next~


	8. Chapter 8

Ash had not underestimated how long it would take to pull himself out of Saffron. 

He simply couldn't get enough of his new wife. But were he so easily seduced away from his journey, he'd not have been the man that Sabrina fell for. 

A week of training, planning, and more sex than most humans were capable of without just outright dropping from exhaustion, they set out. 

There was still a lot of Kanto to see, and over the course of a month the two did just that, searching for anything and everything that caught either of their fancies. 

Many battles were won and prizes claimed, but Ash was unsatisfied in the the options for new pets to add to their harem. He knew of the ninja girl in Fuchsia and a farm girl, but the two seemed too easy for his liking. 

He wanted something new, his time with Sabrina having refined his tastes somewhat. It began to seem like Kanto has been picked dry, and so quickly into his adventures. Seeing this, Sabrina found the solution, directing her lover to the Battle Salon. 

Having peeked into his mind so often, she knew more about what he liked than he did himself. Trusting his psychic mate, he agreed, and the two traveled to the Salon. 

Upon arrival, Ash found himself greeted by the woman named Anabel; though it took Ash a second or two to confirm she was indeed a woman. She was something of a tomboy, far more so even than Misty. Ash loved Sabrina's plump, beautiful body, but she knew from seeing into his mind that he had quite the fixation of tomboys and tomgirls. 

No sooner had Anabel seen Ash however did her face turn as red as the blood from the nosebleed she received. Surprised by this reaction, Ash asked Sabrina if this girl to was a psychic. 

Sabrina shook her head, Anabel starting to explain as she cleaned her nose, “I-I can read people's hearts.. their souls, emotions, their true selves. I-I.. um.. well..” Her blush remained as she welcomed them in. 

Ash didn't fully understand how her powers worked but it must have been intense for such an immediate and powerful reaction. 

They entered the room, Anabel shutting the door behind them. While she may not have been a mind reader, Ash's aura must have told her everything she needed to know and more. 

Once the door was shut, Anabel began to strip down for the two of them. Ash watched with fixation, aroused intensely not only by her body. 

As she removed her clothing, he found that she not wasn't wearing any kind of underwear beneath, but also had ropes tied around her body. They were tied tight, digging painfully into her skin. Ash practically began to drool as he realized he had found a full on masochist. 

As Ash moved in towards Anabel, losing his clothes quickly, Sabrina decided to occupy herself with the pets, seating herself on Richie's member to ride him, pulling Misty to her face by her hips to eat her out while her powers brought dildos to both of their asses, hammering into them mercilessly. Ash pinned the roped girl to the floor, groping her aggressively. 

Anabel shivered and moaned, body squirming as she pressed herself in for more, “F-fuck me~” She moaned desperately, able to sense Ash's intent, the sheer force of his desire. “Fuck me, hurt me, break me like a toy~” She wheezed, her words only pouring oil onto the fire within Ash. 

Ash tested the grounds with the woman, pulling the ropes, pinching then twisting then biting at her small, sensitive chest, even smacking her-albeit gently at first. 

It was amazing, she took all of it and seemed to do so quite happily, a puddle forming beneath her as every painful grab or strike seemed to sent more waves of pleasure throughout her. She was like one of his mothers' well trained slaved. 

“Now, where did such a cute thing like yourself learn to do things like this?” He asked with a grin, curious about what had turned her into such a little slut. 

“I was raised proper and prim,” Anabel explained through her moans, “Treated fragile like a porcelain doll. I wanted freedom and started looking for it. When I found BDSM and well.. its all history from there~” 

Ash listened with delight as he moved into a sitting position, “Then how about I give you what you want~!” He said, pulling the ropes hard to force her body up and into his lap, spearing her down onto his member. 

She screamed in pleasure, cumming instantly from how riled up she'd gotten already. Ash shuddered, thrusting up into her, bouncing the tomboy on his cock roughly, nailed digging into the skin on her hips as he forced her up and down hard. She came a second time fast, then a third. The poor girl must have been pent up for something like this for far, far too long. 

To say Ash broke her easily would be inaccurate. It was more than she'd broken herself some time ago, a slave searching for a master, one who'd finally walked right up to her. 

He began to beat her ass as she rode him, each strike only encouraging her to ride faster, moans filling the room as her tight cunt milked Ash's cock. 

Soon her entire ass had gone a deep red, at which point he moved to pulling hard on the ropes, making them dig harder into her pale skin. He leaned in, biting down hard onto her nipples and pulling them painfully. 

Her screams of ecstasy filled Ash's ears and poured into him like fuel as he hammered up into her. By the time Ash reached his own climax, Anabel was looking down the barrel of her sixth, back arching in pleasure as Ash unloaded into her. The girl slumped off of as onto her back, panting heavily. Ash grinned at her, moving in for a kiss. 

“You're mine~” He told her, stating the obvious rather than suggesting the option, “You'll be my slave forever~” 

The words only seemed to fill Anabel with yet more pleasure. Rather than respond verbally, she rolled over, spreading her ass for her master to use. 

Ash pounced immediately, sinking his cock into her delightfully tight asshole. Ash had not been known for being gentle with any of his pets, but the willing submission of this attractive tomboy seemed to have unleashed the beast so to speak. He hammered into her as though trying to put her through the floor. 

Anabel's eyes became hearts as she sank into an ocean of rough, painful pleasure. She didn't even bother trying to keep track of her releases, though felt it quite intensely whenever Ash reached one of his own. 

Anabel's leg twitched as she was pounded like slab of meat, finding herself unable to think or even maintain control of her bladder, making her cum not the only fluid she was being fucked in a puddle in. 

She was Ash's now, his masochistic maiden. Ash didn't stop until Anabel was passed out; and even then kept going until he could make sure she wouldn't be walking right for awhile, her ass so overfull with his cum that is poured out when Ash's cock was no longer plugging the sore hole. He turned to the others and approached. 

Misty's eyes half glazed from the orgasms Sabrina had given her, gagged as Ash's cock was suddenly buried in her throat, her master moaning as he began to skull fuck her. 

He'd have to find some way to thank Sabrina for bringing him here.  
(

* * *

)   
It was a week before they could leave the Battle Salon; partially because a new maiden needed to be found to replace Anabel, not an easy task on short notice.

Also partially because of how hard Ash had been with her, making her need time to recover before travel was really feasible. But then the same question from before presented itself: where to next? 

It became clear that there was little left for Ash here. Strong as he and his team gotten he wasn't yet quite confident to try for someone like Lorelei of the Elite 4. 

Which left them with only one clear option: find a new region. A week after they left the Battle Salon the group was sequestered in a private room on a cruise ship taking them off to Hoenn. 

They weren't sure what they would find there, but more than eager to find out~


	9. Chapter 9

May and Max Maple hadn't had any idea what would be awaiting them on their pokemon journey. 

They were more nervous to be traveling for the first time than they were ready to admit, which is perhaps why they so readily joined Ash and his friends for a peaceful lunch. It felt good to meet someone so nice right out of the gate, made the wider world seem less scary. 

They talked, had fun, discussed pokemon; the time seemed to fly. The two didn't know when they lost consciousness. But when they woke, they were quite certain things had gone horribly, horribly wrong... Both of them were naked, their bodies tied up. 

Nearby, Ash was sitting down, his pikachu riding his cock, moved up and down faster than the pokemon could probably take by Ash's hands. Nearby him, Sabrina was hammering a strap-on into Richie's ass, her thrusts causing his own member to sink into Misty. 

The two siblings stared in a combination of utter shock and overwhelming fear. The two set to trying to sneak away, trying to wiggle and crawl their way to safety. 

Unfortunately they'd been tied in such a way to make doing so impossible without making too much noise. Even if they hadn't Sabrina would have sensed them easily. 

The group was alerted to their movement and gave them a frightening smile as he spoke, the kind man they'd met before gone, “Welcome to your new life! You two are both going to be my slaves, and serve me for the rest of your lives. Struggle if you want, in fact I'd kind of like you to. That'll make it much more fun~” He moaned, cumming into the pikachu as he finished speaking. 

He set the pokemon and snapped. They must have discussed what they'd do before the siblings had woken, as they all ceased their activities and moved towards the two without a word among them. Ash, Richie and the pokemon to Max while Sabrina, Anabel, and Misty to May. 

“Please,” Max begged, “P-please don't do this! L-let us go!” Richie moved in front of Max with a smile that frightened him nearly as much as Ash's, though his eyes were what frightened him the most; empty, like the lights were on but no one home. 

“Don't worry, you will be happier as Ash's slave~” He said. 

Max recalled learning about the condition known as Stockholm syndrome at hearing this, but couldn't say anything before the boy leaned in, kissing him intensely. Horror flooded all of Max's senses as he was forced into the kiss; his first kiss stolen. 

Richie leaned over Max as he kissed him, causing their members to rub together gently, sending a strange sensation through him. Said sensation was only amplified by Ash's Bulbasaur. His vines moved in, thrusting into both of the boy's, fucking their asses roughly. 

Despite being more than powerful enough to evolve, the plant pokemon had decided against doing so. Ash was glad for this, as it proved him a loyal pet; and made fucking much more manageable. He could feel the vine probing inside him, making his stomach churn as it send an odd stimulation through him. 

When it found the boy's prostate he practically screamed, shaking violently as he came, a pleasure he didn't want but couldn't stop. The vine retreated, giving Max a few small seconds of relief from it all before the vine was replaced with Ash's cock. 

He moaned as Max's tightness as the size of the cock and the force he thrust in with caused the boy to begin sobbing, unable to hold back the tears anymore. Richie giggled, licking the boy's face. 

“I used to be like you, you know,” He said as he moved out from under Max, holding him up between himself and Ash as he brought his tip to the boy's lip, “But master showed me my true purpose~” 

Richie thrust forward, moaning as he began to fuck Max's mouth. He moaned as he spit-roasted the boy with Ash, the two thrusting in sync with him. 

His sobbing grew weaker as his mind became foggy, the exhaustion from the several orgasms his body was forced into taking a toll on him. Anabel, seeing this, grinned and moved down beneath Max, positioning herself so his member was forced into her pussy as he was fucked. 

Max groaned, the pleasure a small reprieve from the horror he was experience, though if anything it only helped him break faster. 

Ash smacked his cute ass as he hammered into it, feeling his ass grip tighter around his cock with each climax, making Anabel shiver as she felt it. “Can I keep him as my pet master~?” Anabel asked. 

Ash smiled, nodding, “For my favorite masochist? Of course~” He said before pulling Richie into a kiss. 

The two thrust harder into Max from either end, unloading into the thoroughly broken boy on both sides, flooding his body with their seed. 

A brand new broken cock sleeve, just like Richie; albeit perhaps even farther gone than he had been. Anabel kissed her cute little pet as she positioned him on top of Ash's Nidorino's cock. 

She slammed his hips down, giggling at how he whimpered before starting to ride the poison type as Ash's Nidorina in turn began to ride him, the boy practically fucked into putty between them. Nearby, Max's sister was gritting her teeth desperately. 

Misty and Sabrina had been teasing her relentlessly while Ash's Charmeleon thrust up into her ass, her plump breasts bouncing with the movement. The stimulation should have made her cum by now, but Sabrina had been making sure she couldn't. 

Ash approached her with a smile, lining up and rubbing his member against her pussy, “Don't worry, you'll be happy soon~” He said, leaning in to kiss her before slamming into her so hard the force hilted Charmeleon inside her ass. 

She squealed into the kiss, body writhing between them as the two plowed into her mercilessly. Her tits only bounced harder from the sudden boost in pace, Ash reaching up to grope them greedily. 

May wanted to resist, wanted to willpower her way through it. Her teeth were grit so tightly they were liable to crack. Seeing her brother broken and being fucked like a toy between two pokemon broke the last thread she had. A human's mind and body can only take so much no matter who you are, and May was well passed her limits. 

When Ash pulled back from her lips, May heard the words she was saying before she could think to say anything, feeling like she was falling into herself, all control of herself, all sense that she was even her, evaporating. 

“M-Master.. please.. f-fuck me more.. I-I need to cum!” 

Ash grinned, giving Sabrina her cue. The teasing stopped, Sabrina's hold on her releasing. The damn burst instantly, a scream erupting from May's mouth as she came harder than she thought possible to cum, whatever was left of her leaving her with the noise. 

Ash slammed back in to the base, the Charmeleon doing the same. Both of them came, bloating May with hot, thick seed and instantly triggering a second release. The girl was given no time to recover, that she'd ever fully do so. 

No sooner was she pulled from the Charmeleon's cock was she dropped onto her fours, her ass split now by Ash's cock rather than the Charmeleon's. May's cry was cut off by Sabrina's strap-on slammed into her throat, Sabrina forcing her head down to skull fuck her. 

“You'd better appreciate this bitch, my husband's cock deserves something to take it like a nice, good little slut~” She grunted with the force of her thrusts. 

She leaned in, Ash doing the same. The two made out heatedly as they fucked the girl between them, their kiss loving like a couple on their honeymoon. The scene around them grow only more heated from there. 

Nearby the Nidorino and Nidorina only got rougher, both having been desperate for someone to dominant for quite some time, a nice cute little boy for him to stuff and her to milk was just what the doctor ordered. 

The Charmeleon moved to play with Misty, the Bulbasaur joining her. She was on her back, plowing into Misty's ass just as roughly as he had May's, Misty's mouth occupied by the Bulbasaur's while his vines probed deep into her pussy. 

The Pikachu and Butterfree decided to have their fun with Anabel. The bug type had landed on her head, the girl licking heatedly as her small cunt while the Pikachu thrust aggressively into Anabel's, letting out small shocks into her that she seemed to love, getting wetter and squeezing tighter with each painful shock. 

May's tits were used like handlebars as master Ash and mistress Sabrina plowed into her. 

The moment was beautiful, practically perfect. Hoenn was a brand new region for Ash to enjoy, just full of sluts for him to find and break. 

And like his mothers had taught them, he was going to catch them all~


	10. Chapter 10

With the new sibling pair in his group, Ash set off towards the town of Rustboro. 

He was excited for surprises certainly but wasn't about to just tear off through a region without a plan. He could have found himself with all duds in his adventure if he did that. So Ash and Sabrina had done a little research before setting off proper, and decided on a certain school teacher to be their first target. 

She'd do quite nicely indeed~ but Ash would need pokemon of this region as well. And just Ash's luck, one such pokemon brought itself to him. As they walked down the path, the green bipedal pokemon jumped from the trees and landed before Ash and the group, evidently challenging him. 

Ash grinned, sending his Nidorino out against Treeko, who realized very swiftly he may have bit off more than he could chew. 

Even without type advantage it was a walk over, powerful kicks and a sharp horn attack sending the Treeko ass over tea kettle into the trunk of the tree he'd jumped from. Ash threw a pokeball, capturing the grass type. 

He patted his Nidorino's head, careful to avoid the spines as he praised him for thoroughly kicking the pokemon's ass. But the Treeko's ass was about to have much different issues, and so with a smile, he let the pokemon back out. 

The formerly cocky Treeko collapsed onto his fours, panting heavily to recover his breath. Before he could even do that however, his eyes went wide as he felt his new trainer's ass forcing itself deep into his ass. 

The grass pokemon thrashed and struggled, but even if he weren't already weak from the battle-if it could have even been called a battle-Ash's strength and weight alone made him too much for the Treeko to fight off. 

Especially with Ash's cock hammering into his formerly virgin asshole and doubly so with the Nidorino making use of his mouth, thick, rough cock hammering into him so hard his body smacked against the pokemon's face, the only smell he experienced an intense musk and the only sound the moans of the two. 

Soon... his body couldn't handle it, going slack between the two. This didn't stop them of course, nothing did until they'd both cum; and even that didn't give him much reprieve. After his throat and ass had been pumped full, Ash set his Bulbasaur onto the the Treeko. 

The bulb pokemon grinned, vines stretching out and dragging over the Treeko, intent on giving him a proper training~ Ash chuckled as he watched the grass starter dominate the other, vines striking his ass and chest. 

Ash stroked his cock to the sight, considering to join him again; though before he could, the sound of humming drew his attention elsewhere. 

Following the sound, he found a Roselia. The plant pokemon was dancing off the path, humming musically to herself. Grinning, Ash continued to stroke himself as he called for his Charmeleon to take her down. 

If the Treeko had hardly been a fight, this was hardly even an encounter. A single rush of fire had the flowery pokemon stumbling, barely conscious. 

She was hardly certain what had happened until she felt herself being lifted off her feet, the Charmeleon facing the Roselia towards Ash as his hot, scaly cock slammed into her ass. 

The grass pokemon screamed at full volume, writhing to trying and escape. Even if her lightweight body could have flailed its way out of the fire type's grip, Ash soon joined him, cock ramming into her cunt with a grown of pleasure. 

Charmeleon bit her neck and shoulders roughly as the two double teamed her, cocks hammering in from either side, the difference in size making her body stretch in ways it was definitely not meant to. Ash was certain such a thing couldn't feel good, but it felt amazing to him and Charmeleon~ 

The two couldn't even consider stopping. They came together in unison, groaning as they flooded her with thick, hot cum. 

The Roselia screamed out, body growing tense as the stimulation forced her to cum as well. The fragrance that the grass pokemon let off always came from whatever they were taking in, hence their more pleasant smells coming from clean, fresh water. 

In such a state of intense stimulation, the poor thing lost all sense of herself, her body taking over like instinct, taking the cum filling her and using it for the pollen. 

Rather than simply smell nice, the thick green dust that practically burst off the Roselia was effectively an aphrodisiac. It spread throughout the area, the others all inhaling the dust. 

All those that did began to sweat and shake, not simply horny but horny for the Roselia herself, wanting.. needing to fuck her. Ash slid out of her pussy, moving behind her and slamming into her ass. 

The Charmeleon hadn't pulled out, the two hammering into her tight-even tighter now-hole together. 

Her screams grew louder, but her pollen made her situation so much worse. Richie and Max joined them, lining up to her pussy together and drilling into it together just as Ash and Charmeleon were in her ass. 

They moved onto the ground, Max and Richie on their backs as the massive, groaning fuck heap grew larger, Sabrina burying the plant pokemon's face between her legs, her psychic power aggressively groping her sensitive areas to drive the Roselia even more wild as she ate the gym leader out. 

And still more joined, Ash's Pikachu taking one of her arms and thrusting into her plush, soft flower petal hand, moaning heatedly at the feeling like Anabel locked her legs around the other arm, letting the rose thorns dig against her thighs as her pussy ground against her body. 

Even if that first round of fucking hadn't been enough to break her-which it most assuredly was, the cocks alone shattering her entirely and the humiliation of everything else mere overkill-she still wouldn't have made it. 

With her mind effectively pudding she couldn't stop her body converting the cum into lust inducing pollen, driving them more wild with each burst.

It wasn't as many as that first intense round, some needing breaks to recover, only Ash remaining throughout the processes. 

Sometimes it was just him, sometimes two others sometimes more. Round after round, orgasm after orgasm. It was hours spent on that trail, raping the Roselia like it owed a mob boss money. 

Ash was the last to unload into her, pumping her cunt full one last time before sliding out, finally able to think. The wind had blown enough of the pollen away for everyone to recover. 

The Roselia was cum soaked through and through, so full she looked like a cum balloon and so covered she barely looked like a Roselia. 

That pollen, Ash thought, listening to the moans and wails and screams, sounds of sex and of fleeing from the wilderness around him that had also been effected, could be quite useful~ 

In any event, the group needed time to recover before they carried on, having lost quite a bit of daylight. But it wouldn't be their last interruption. 

The Ralts was an.. interesting case. The Emotion pokemon had most certainly sensed him as he approached her, and had most certainly sensed his intention for the cute little pokemon, what her innocent look flared up inside of him. 

And yet she did not flee. Perhaps she simply knew she couldn't, not having teleport at her level, but she seemed so calm as Ash approached her, didn't struggle or even cry out as he pounced her, pulling her off the ground and slamming her onto his cock. 

Well, she did cry out then, from the feeling of the much larger trainer's thick cock spreading her tight, small cunt. 

He grunted as he forced her hips up and down, throbbing inside of her lovely body. He knew that she would go from cute to beautiful with her evolution, but the destruction of such an innocent looking girl was quite the satisfying sensation. 

The psychic type seemed to break like hot glass falling into ice cold water, her above average powerful mind paradoxically yielding instantly to the assault. 

Sabrina explained to Ash as the pokemon's stomach bulged from the size of the member slamming into her small body, that the psychic had already bonded to him, and once a Ralts does such a thing, they prioritize their trainer's happiness and saftey above their own lives, something that stays with them the rest of their lives. 

Essentially, she was broken the second Ralts sensed Ash approaching, before he'd even laid eyes on her. “She only bothered with letting you pounce on you because she knew that you'd still want to.” 

Ash found this deeply amusing, his pace only growing more intense. He'd known vaguely that the pokemon bonded emotionally of course, but hadn't realized how intense such a thing was. 

“Strange though..” Sabrina says, an eyebrow raising as she seemed to sense something, “She didn't just bond with you..” 

“Huh?” Ash questioned, grunting as he pounded the tiny psychic. 

“Just before you, her mind must have reached out to Anabel first. It wasn't lone, but enough for some of Anabel to imprint on her.” Ash was still slightly confused by this, so Sabrina, grinning, brought her hand down hard on the Ralts' ass. 

She cried out, Ash feeling her pussy squeezing tighter around his cock as she came. Ash grinned, finally understanding it. Anabel's masochism had imprinted onto the Ralts~ Ash gave her a similar smack to the ass, then another; then proceeded to beat her tiny ass red as he fucked her. 

By the time he'd finally cum, unloading into the little thing, she'd cum a total of five times herself, leaving her limp with a twitching leg. Were her eyes visible they'd certainly be glazed over. 

Ash kissed her dominantly before catching her officially and setting up camp for the night. 

Once their camp for the night was set up, Ash relaxed against the ground, he pulled up May's Torchic, bringing the little fire type down onto his cock. He groaned, pumping her up and down his cock like a pocket pussy. 

Like Charmander, he found the Torchic's body remarkably warm inside, though even tighter around his cock, making her an excellent cocksleeve; something that his Charmeleon quite agreed with, both intent on keeping her as their official fire type fuck toy after she evolved. 

As he pumped the Torchic, he watched Max and Anabel played with Max's Poochyena, the little dog between the two, Max's cock hammering into her cunt as her tongue worked between Anabel's legs. 

Both moaned happily as they indulged. Richie had been right about how quickly Max would break, and Anabel's 'Little Toy' as she'd grown fond of calling him, happily did whatever his superiors asked, be it taking it or giving it. 

Ash grunted, pumping the well broken Torchic along his cock like a literal toy until he'd milked one last climax for the day out of himself. 

He sighed happily before passing her off to Charmeleon. He normally would have been happy to go at it long into the night with his many pets, and likely would still have a round or three with his wife, but the Roselia encounter had drained quite a bit out of him. 

More than that though, he had something important to get started on. Shortly after he'd arrived in Hoenn he'd received a package from home. 

His mothers had correctly guessed he'd be missing the taste of the milk that their Milk Maids produced. That had considered bottling some and sending it off, but then had come to a better conclusion. 

Ash grinned ear to ear as he opened up a package containing syringes, drugs, Miltank milk and everything else Ash would need to turn a normal woman into a Milk Maid. He'd have one all his own. 

He went back and forth on who to use it on before deciding ultimately on May. 

He was more than happy with Anabel as she was, he knew from lessons as a kid that it didn't work very well on pokemon, and Misty.. well.. it came down to essentially just preferring the idea of May with tits twice as large as they were now, producing the milk he'd grown up loving. 

Sabrina teased her lover, seeming rather certain that his choice was motivated by wanting to keep Misty an alluringly fit tomboy. Ash blushed but didn't argue. 

He'd learned swiftly after meeting Sabrina that trying to do such a thing to someone who could literally read not only your thoughts but your subconscious was perhaps the literal definition of pointless. 

The process would take awhile, May wasn't going to wake up a Milk Maid of course. But he figured that now was a good a time as any to get the ball rolling, injecting her with the first of the Ditto/Eevee derived chemical into May. 

While her body adapted to milk, he could turn his focus onto their current mission: Roxanne.


	11. Chapter 11

Roxanne was a smart woman, and a strong trainer. She was a gym leader after all, and a teacher at that. Definitely above par as far as trainers go. 

And yet here she found herself, spit roasted by two people she'd met mere hours earlier. Ash's cock was splitting her asshole apart while Sabrina's strap-on fucked her throat without mercy. Cum was leaking from her pussy from being filled repeatedly, forming a thick white puddle beneath her. 

She'd cried throughout it all, and sobbed even now. But even as the lines of tears stained her face, she could feel her body starting to enjoy the treatment...   
(

* * *

)   
It had started with a battle in the gym. Manning her post, Roxanne hadn't thought anything of it as Ash entered for battle. 

Though he didn't have a single local badge, she opted to fight with her full team of six, usually reserved for those who had seven or more badges. He was strong, more than up to the challenge, she was sure of it just from seeing the Nidoking. 

Ash had recently gotten his hands on the moonstones needed for evolving the two of them, making them even more powerful. Her two Golem dropped like flies to the Nidoking's fighting attacks, and its Probopass didn't last much long, though it got a decent amount of damage landed, as did the Magcargo. 

Her second to last pokemon, an Aggron, finally brought the Nidoking down, but his Nidoqueen swiftly made short work of both it and Roxanne's ace, a Rhyerior. 

The battle was over in record time, the gym leader's jaw practically hanging open. She was thoroughly impressed, and more than confident in her choice to present him with her badge. 

As he shook her hand, another woman walked open, “This is my wife Sabrina,” Ash said, “We heard you were teacher as well as a gym leader? Could we possibly see your school? We've been considering settling down in this town you see, and may enroll our children.” 

Roxanne smiled, nodding. She left her pokeballs in the healing terminal to recover from the battle as she lead the couple to the school built into her gym. Ash and Sabrina's harem was currently waiting in a hotel room across town, Sabrina having figured it would much better if they appeared like something approximating a normal married couple interested in the town, which was proving quite true. 

They talked together, Roxanne discussing how she taught, how she'd trained to be a gym leader, about the town itself, etc. It was a very pleasant air. Ash felt it change before he knew what was gonna cause it. 

“Yes, I do just love my students.” Roxanne said warmly. 

Sabrina smiled and spoke without hesitating, shattering the pleasant mood in an instant, “Because you want to have sex with them all yes?” 

The school was soundproofed from the gym to avoid students getting distracted, so when the room went silent, it went truly silent. Ash raised an eyebrow. He'd known the plan was to exploit whatever her mind was hiding, but hadn't been expecting that of all things. That was more than enough ammunition~ 

“W-what? How could you even say such a thing!? Not only would that be illegal but morally-” 

Sabrina cut her off, voicing the scenarios Roxanne had fantasied, dreamed about, masturbated to. She went silent, face going from ghost white to cherry red as the psychic described with perfect precision the details of her deepest, most depraved fantasies. 

“Now, now, now,” Ash said with a grin, “I wonder what would happen if this got out~” 

Ash knew, Roxanne did as well. Mind readers weren't common in Hoenn, but they were known to exist of course, there was a psychic gym after all. 

Roxanne realized that this woman was one such person, and realized just as quickly that it would only taken a second psychic to verify what she'd read for words and thoughts alone to have her stripped of her titles, of her job, and potentially be throne in prison if they felt she'd ever act on her fantasies. 

And lord knows what would happen to her there... 

“..w-what do you want from me?” She questioned. 

Without words, Roxanne was forced onto a desk, her clothing practically ripped from her body. Ash took out his member, already stiff with anticipation. The sight of it widened Roxanne's eyes and dropped her jaw, “Th-that thing will tear me apart!” 

This earned her a smack across the face and an amused giggle from Sabrina, “I suppose you'd prefer it if it were small and inexperienced huh whore~?”

Roxanne bit the inside of her mouth, and didn't argue as Ash lined up to her, Sabrina moving over top the gym leader. 

“Lets see if I can break you of your bad habits~” He said. 

The statement was admittedly on the far end of hypocritical, but Roxanne didn't know that and wouldn't until she was too far gone to even realize it. 

He slammed in suddenly, the rock trainer screaming out in pain, her cunt gripping tight around Ash's cock, practically milking it as he pumped into her. She was extremely tight, forcing Ash to move slowly for the first few thrusts before finally ramming to the base inside her. 

The intense sensation flowing through her caused her to cum almost instantly. She'd avoided sex altogether to keep her mind off of her fantasies, and as a result had almost no tolerance for sex. Ash grunted as he pumped into her, keeping the pace rough and aggressive now. 

He moaned into Sabrina's mouth as his wife kissed him, her psychic energy groping Roxanne's chest, squeezing her tits and pulling hard on her nipples. 

The desk rocked hard with the force of Ash's thrusts, the room filled with her cries and the rocking desk, but with the room soundproofed, there'd be no one to come to her rescue. 

Roxanne lost all sense of time, cumming again at some point from the titan of a cock pounding into her. Ash groaned, unloading into her. Roxanne's entire body shook, but even as she felt the burning hot seed pumping into her, she was relieved; believing that it was finally done. 

This belief melted away as Sabrina got off of her, Ash lifting her off the desk and bringing her to the window. 

His chest was to her back as his cock plunged back into her, her tits pressed against the window showing outside the building, her legs open giving anyone who happened to be passing by a wonderful view of the thick cock plowing into her from behind. 

She gasped, “N-no! People will see! You can't let them s-” 

She was cut off by a firm strike to her ass, “You probably want everyone to know what a slut you really are~” Ash groaned as he fucked her against the wall, not only not stopping but picking up the pace. 

He bit down on her neck dominantly as he pounded into her. Roxanne sobbed as her pleas were ignored, but her body betrayed her, gripping tight around Ash's cock as she came and not only once, juices running down the window in such amount that it would be obvious to anyone watching that she was swimming in ecstasy, be it against her will or not. 

Her body shook as a second load of Ash's cum flowed into her, just as hot as the first. Her body tired and her mind humiliated, she prayed they were done now; only for Ash to slam her back onto the desk, this time with her on her stomach. 

Looking up, she saw Sabrina sliding a strap-on with a member on both ends into her pussy, shuddering gently as she felt in before lining the toy tip up to Roxanne's lips. As his wife lined up to her mouth, Ash lined up to her ass; though the gym leader didn't notice this until the searing pain of her ass being forced apart burned through her body. 

Her scream was instantly muffled as Sabrina thrust in, moaning heatedly as her thrusts into the girl's throat stimulated her cunt through the toy. Her sobbing returned, even harder this time. 

Ash was equal parts aroused and slightly frightened by how the woman's sobbing face only seemed to make Sabrina hornier, her hips speeding up like she was trying to force the fake dick into Roxanne's stomach. 

Ash would need to find the girl a direct bitch to play with before he woke up with his own ass being plundered; though whether or not he'd be alright with that from her is a thought he pushed down so fast he hoped Sabrina wouldn't have noticed it. 

Roxanne still begged for mercy, or tried to anyway. With her throat stuffed, her attempts to speak only resulted in her gagging and sputtering, literally choking on the strap-on. 

“Hm? What was that~?” Ash questioned mockingly as he smacked her ass again, a red hand print starting to form. 

“She wants it harder~” Sabrina told Ash through her moans. 

Ash grinned, picking up the pace, slamming even harder into their trapped bitch. As they spitroasted her like a stuffed pig, it occurred to Ash that Sabrina could have been joking or lying about that, but he was honestly aroused either way, pulling Roxanne's hips hard as he thrust forward, hammering her as though trying to meet Sabrina's tip with his own inside the woman.

Her mind fought it, struggled to remain whole, but her body was stronger, and it was in heaven. A hellish, sinful heaven perhaps, but heaven nonetheless. She came violently, and by the time Ash let loose into her ass, they realized that their new slut had passed the fuck out from the stimulation. 

Sabrina seemed more than content to keep using her in the meantime though~ It was much later when Roxanne woke, Ash and Sabrina already dressed while Roxanne was still naked and caked in cum. 

“Some day I''ll have a home, with many children,” Ash said with a smile, “You will be one of my slaves. You will be the teacher to my children. Understood?” 

She nodded without hesitation, eyes and mind vacant. As Ash brought his cock to her mouth she kissed it lovingly, “Yes Master~” She purred. 

They left, leaving Roxanne to realize that they'd taken her clothing with them, so getting cleaned up and more so getting home without being seen would be something for her to deal with. It wasn't their problem; nothing in this town was really. And as such, the whole group was gone by the next day. 

There was no worry whatsoever of Roxanne going rogue, they had too much on her even if she wasn't thoroughly broken. Before they left though, Ash stopped to send his Nidoking and Queen as well as his Butterfree and sent them to his mother's lab. 

They were powerful and good companions to have around. But he wanted to focus on this new team as it developed. The Ralts had become a grade A slut due to her mind connecting to firmly to Ash's desires and would become even more so as she evolved. 

The Roselia had discovered surprisingly good cock sucking skills, and was somehow still remarkably humiliated by people fucking her petal hands despite being broken, perhaps something innate to them. 

Regardless her protests if anything encouraged the others to do so more frequently. Ash glanced to his Charmeleon as they walked down the route, the Torchic bouncing on his cock as they walked. 

He wanted to evolve the fire type soon for some more power, but as he considered powerful fire types, his mind drifted to his next target~


	12. Chapter 12

It took longer to get from Rustboro to Lavaridge than Ash would have liked; especially because of the lack of any targets in between. 

The only gym had been that of a man and not one of Ash's types. Perhaps it had simply been bad luck but there had been no common trainers he nor any of his pets had been fond of. 

He apologized to Sabrina for having taken this path, but she waved it off. Neither of them were native to this region and the other path was likely to be just as barren for all they knew. And the journey hadn't been fruitless. 

Along the path, Ash had captured a Sneasel. She was a good pokemon, fast, agile, and fiercely intelligent; so much so that its evolution even had a written language. Being part dark type the pokemon had something of an innate deviousness to it, something that her nice frame made all the more pleasing to Ash. 

May had progressed further along the Milk Made process, the Eevee/Ditto solution making her physiology unstable, adapting to the vast quantities of Miltank Milk, integrating it into her biology to allow her to produce it. 

She wasn't fully there yet, but her breasts had already grown quite a bit as they filled with the sweet drink. Beyond these though, the trip had been the biggest pain in Ash's ass since arriving in this region. 

It was for this reason that his arrival in Lavaridge was met with a cry of, “Fucking finally!” so loud the locals likely assumed him a crazy person; something that was quite up for debate admittedly. 

They were so exhausted from the harsh trip they had taken that there wasn't even any sex that first night. Just showers and sleep to rest their muscles, sore from the last three days of hiking through valleys of rock and steel types. 

There would be fun tomorrow, but Ash's mothers had-shocking though it sounded-restraint. He wouldn't even enjoy it if he attempted tonight. Sabrina curled up with her husband, the two holding each other through the night. 

While they did still occasionally battle for dominance in bed their promise to be proper lovers had not been an empty one, and it felt good to simply hold one another. Ash wondered how his mothers were doing as he drifted to sleep with his wife. 

The next day, rested and in a better state of mind, Ash was able to say with confidence that Flannery was worth the trip. 

Body type similar his lover Sabrina with large pale tits, a plump ass and hair so red it could only be growing out of a fire type gym leader. She was cocky to, which was rather amusing. 

He admitted she was strong, but his Kirlia's psychic power had grown quite powerful, making short work of most of her pokemon. He honestly may have been able to sweep with Kirlia, but he took some amusement in watching his Pikachu finish the battle against the Torkoal. 

Ash accepted his prizes and was fully prepared to force himself onto the gym leader there and then, but he was stopped by her speaking. “Nice battle. Wanna try the spas with me? 

Always helps me relax after a nice battle.” She said, stretching her arms over her head in a way that puffed out her chest. 

Deliberate or not, it peaked Ash's interest, and he happily agreed. He gave Sabrina a thumbs up to inform her this one would be solo. She nodded, giving him a grin as she returned to the hotel while Ash followed Flannery. 

They arrived at the spa together, Flannery putting her pokemon away to rest. 

She'd be alone, which was good. While Ash was pretty good at outplaying pokemon, fire, ice, and ghost were the only he had no real good counter play against, not without preparation at least. And while this did mean taking her with the same brutality he had so many others, he decided against it. 

As the two slipped into the hot spring together, he opted for the more careful approach. They both sighed as they relaxed into the water, but neither was merely relaxing into the water. 

While Ash's eyes were certainly wandering over Flannery's milky skinned body, her own were likewise admiring Ash, lingering a bit too long when she saw the size of the length he was sporting. 

“Damn, not bad.” She said, somewhat flirtatiously as she scooted closer to Ash in the hot water. “Flattering coming from you~” Ash said with a smile, likewise moving closer to her. 

This woman, Ash had deduced, didn't have a lot of time for very much fun, and must not have in some time. 

This put her right where Ash wanted. 

He moved closer still, but rather than forcing a kiss or pouncing there and then, he simply moved yet closer, knowing that it would be better if she was the one to push it. 

'You were blessed with two heads Ash,' Delia had told him, 'And you shouldn't try to use the lower one for everything.' 

The expression had always made him snicker, but he knew it was all too true. Blushing at how close they had gotten, able to feel his body heat even in spite of the hot water. 

To relax herself, she leaned in, tracing a finger along his muscled chest, “Bet you get all the girls with this~” She teased, “Guys to I'd reckon.” 

He smiled, bit said nothing as he leaned in to kiss her, Flannery blushing, but leaning in as well as he did, returning it gently. She was in his grasp now; a phrase that became literal as his hands worked up her body to her chest, groping her gently. 

She could, as far as she believed, pull away. But she didn't. She didn't want to. His hands moved down to her hips, pulling the gym leader into his lap. She bit the inside of her cheek, knowing where this was going. It had been too long, she wanted it; and with Ash's overpowering presence, she felt she might just need it. 

Ash's hands moved to hold Flannery's ass as he lined up to her pussy. She was in his control now, and she liked it; though she did wish she'd told him to start slow, as the next motion hilted him inside her hot, needy cunt. 

She started to scream, but Ash's kiss muffled it. Flannery groaned hard, knowing she was in for one hell of a ride. She bounced on his length, at first only from the surprising force of his thrusts up into her. 

She managed to adjust eventually, holding onto him and starting to move her hips to match his pace; if not the intensity of it. Ash leaned in shortly after she did this, latching on and sucking her tits heatedly. 

The pleasure, more than she'd gotten all at once in longer than she was willing to admit, filled her mind like magma, melting her thoughts. And fucking in the hot spring only seemed to rile her up even further; like a literal bitch in heat. 

Her legs locked around Ash as their hips smacked together hard, creating waves in the hot water. 

Flannery came fast, but surprised Ash at how well she took it, hips not even slowing as she kept going, wanting more. She came twice more as she practically fucked herself with Ash as a toy, milking his cock lustfully. 

Her moans were likely echoing out and being heard but she was in too much carnal pleasure to care or even consider it; until her partner came and returned her into reality. She cried out hard at the unfamiliar sensation as he unloaded deep into her. 

She started at him in shock, needing a moment to recover before she could indigently question, “W-why didn't you pull out!?” 

Ash responded with a rough smack across Flannery's tits before forcing her around, “Because you're mine now~” he growled, slamming into her ass with the same force he had her pussy. 

Flannery's mouth opened, but nothing came out. She'd been a virgin back there, and the pain was too intense for her to even properly process as it happened. Ash bend her over, leaning over as he grabbed her breasts like handles, hammering into her poor ass. 

He chipped away at her for hours, relishing the sensation of finally breaking someone new for the first time in months. He bit hard on her neck to mark her as his cock molded her asshole, pumping burning hot seed into it and only stopping for moments before picking up again, pounding her relentlessly. 

He forced her to stay conscious with unwanted pleasure and unprecedented pain until finally the last of her thoughts melted away fully. He had plans for her, especially that chest of hers. 

“You'll make a good milk maid to~” He purred, “You've got a month to find a replacement gym leader. Got it?” Flannery nodded, ass full and eyes as blank as her mind. Ash smiled, happy with these results. 

He had one more target in this region, then he would be on to yet greener pastures; almost literally given his two new milk givers.


	13. Chapter 13

It had been two months since arriving at Lavaridge. 

The first month was spent training, relaxing, and fucking; primarily in the hot spring. It had been a lovely time all around, but he knew it would be time to head out soon. Around the one month mark he decided to set off towards Mossdeep City. 

The trek was going to suck similarly to the trek to get to Lavaridge; due in part to the fact that he couldn't take Flannery with him. She'd been unable to find a suitable replacement for her and had legal obligations at the gym she wouldn't be able to get out of. 

Sabrina confirmed that it wouldn't be wise to force her to leave, and with a sigh, he agreed to set off without her. 

He took solace in the knowledge that he need only say the word and she'd come to him, and by the time he returned she'd likely be well into her transformation into a Milk Maid. 

He wondered how he would explain the physical change to those around her, the thought giving him a chuckle. In any event, he was off towards the next gym. And he had been right, the trip had indeed been rather shit, if less so than the trip through the mountains. It took a month in total, but they finally made it to Mossdeep, containing the twin psychic gym leaders. 

The trek had had its highlights of course. Ash's Treeko had evolved into a Grovyle, and his Ralts into a Kirlia; who nearly brought their trip to a grinding halt, as Ash was rather compelled to stuff her every second of every day. 

Thankfully Ash had more resolve than one might assume and managed to keep the group moving forward despite his desire to stop and continue plowing into the Kirlia. There'd be time for such things later of course. 

Sabrina had caught a Ralts herself as well. A male Ralts that she looked at with eyes Ash was sure matched his own when he found a new cum dump. It was amusing to see them on his wife as well. 

The most valuable catch of course had been that of a Milotic. Ash was in awe, both of the fact that he'd actually found one in the wild and just from the sheer beautiful sight of the graceful pokemon's movements. 

Sabrina held the elegant pokemon in place with her psychic power as Ash moved in on it. He grinned as he felt along her soft, tender body. His hands found their way to her sensitive entrance. He lined up to her and sunk inside her. 

She felt so different to the pokemon Ash was used to, but amazing nonetheless. Ash had no idea how long he fucked the beautiful dragon pokemon, only that when he was done, she had fully submitted to his will; slithering down to clean his cock without even being asked to do so. 

During the trip May's body had moved further along the processes towards that of a Milk Maid. Her breasts had grown even larger than before, and were starting to give milk. She wasn't there yet, but she was well on her way.

Anabel had trained Max to be quite the loyal pet for her, having commands followed without needing to explain what she meant. 

Richie and Misty seemed to be going at it together more lately when given free time by Ash; to the point that Ash wondered if they might not be becoming a thing. 

If such a thing was even possible for their shattered minds that is, a thought that made Ash chuckle. Ash had yet to find anyone he truly loved and respected as much as Sabrina, nor she anyone that matched her feelings for Ash. 

They doubted they ever would of course. That kind of love wasn't something you found often, and the longer they were together, the more they wondered if they might make their names of 'husband and wife' less of a title/cover and more literal. 

That could wait however, they still had work to be done. And with their arrival at the Mossdeep gym, they had two fresh targets. Tate and Liza were adorable little things, about Max's height and with decent curves on Liza to boot. 

While Ash stepped forward to battle them, Sabrina fell back and set to reading their minds. It was harder than would be with most, but ultimately still child's play for someone like Sabrina, who could create whole pocket realities if she desired. Her eyes widened as she looked through their thoughts, nose nearly bleeding. 

She didn't interrupt Ash's battle to tell him, instead moving to inform the pets and let them in on a plan she'd cooked up with the new knowledge. 

Tate and Liza were a good tag team, but Ash's Milotic and Grovyle made short work of them, winning the battle easily. 

Ash accepted the gym rewards, only to be surprised by the harem surrounding them. He'd not ordered them to do so, and so could only assume Sabrina was up to something. When she spoke, he knew this to be the case. 

“I must say, I'm not surprised you two work so well together,” Sabrina said, “Considering you love each other *that* way to~” 

Ash smiled as the twins went wide eyed and red faced. “I-I don't know what you mean.” The two said nearly in unison. 

“But of course you do,” Sabrina said with a chuckle, “How Tate just loves your fingers in his ass Liza, and how you like the way he plays with your chest~” 

Their mouths opened again to deny it, but no sound came out. The recognized who they were looking at now and knew that denying it would do nothing. They were frozen, and did nothing as the group moved in on them, tearing away their clothes. 

Sabrina, Richie, and May pulled Tate to one side while Ash, Misty, Anabel and Max took Liza. 

Liza was terrified, whimpering as Max leaned in to kiss her. She'd never kissed anyone but Tate before and her body shivered as Anabel and Misty moved to either side of her, kissing and nibbling on her tits. 

Her whimpering turned into a few soft moans, followed by an intense scream as Ash slammed into her. She'd only ever been with her brother before, so feeling something so much bigger that fast hurt worse than anything she'd ever felt in her eyes, her eyes bulging and filling with tears. 

Max giggled, whispering into her ear as she'd been ordered, “You have a cute face when you get fucked~” 

Perhaps it was the words Sabrina had so carefully selected for him, maybe it was the over stimulation, but she came near instantly, sore cunt gripping even tighter around Ash's cock and soaking it. 

Ash grinned, holding her hips as he proceeded to plow her as he did all his pets, ignoring her screams as she felt certain she was going to need medical help after this. 

Her stomach bulged from the size difference, and Liza was quite certain that wasn't good; though the sight of it only seem to urge Ash onward, hips smacking into her harder, driving his cock into her with such force she wondered if he wasn't genuinely trying to break her in two. 

She knew now that begging him to stop was pointless, so instead pleaded for him not to cum inside her. This was met with a smack across her face so hard her vision went away for a second and was filled with stars when it returned. 

“Do not tell Master what to do.” Misty hissed, biting down hard enough on her nipple to nearly draw blood. Liza screamed out again as she felt Ash unloading into her, filling her tight cunt as she sobbed. 

Max simply licked the tears from her face and whispered, “Don't worry, soon you'll love Master's cock more than you ever loved your brother's~” 

She wasn't sure what horrified her more, the statement of what they were doing to her, or the idea that they could actually succeed. She turned her head and saw something that made the scene so much worse. 

Her brother was in no better a state than herself. Richie was fucking his throat so hard Liza wondered if he could even breathe. May was riding his cock aggressively, fat tits bouncing as she took his smaller rod, Sabrina between his legs sinking her strap-on into his ass. 

He too was sobbing, having been positioned in such a way that he too could see what was happening to his sister. 

The idea that his sister was being hurt mixed with the anger and jealously of anyone touching her other than himself burned in him, only to be drowned by the sheer hopelessness of it all. 

The sound of Liza's sobbing was silenced the same way as her brother's, Max thrusting into her throat and setting to fucking it like no tomorrow; confirming for her that if her brother could breathe, he couldn't do so easily. 

Sabrina giggled at this, sliding out of Tate and moving to Liza as Ash moved to Tate. Liza's gags and sobs around Max's members were met now with a muffled scream as Sabrina slammed into her ass. Tate's entire body tensed as he felt the cock that had defiled his sister stretching out his walls by force. 

Richie and Ash enjoyed Tate's body, rutting him from either side like the mindless fuck doll he'd soon enough be. Ash grinned as an idea came to mind. He allowed Richie to unload into Tate's mouth, and after Max did the same with Liza, Ash picked Tate up, Sabrina doing the same with Liza. 

They kept the twins on their respective rods as they stood, fucking them with each step as they carried Tate and Liza towards one another. 

“Lets reunite them shall we~?” Ash said. Sabrina grinned as they pushed against one another, pushing Tate's cock into Liza as they were both still fucked from behind. Both whimpered, wheezed, not even having the energy to cry anymore. 

Though it felt good to be against one another again, to hold one another, to kiss each other, it was all muddled, their minds weak. Still stretched from Ash, Liza could barely feel her brother inside, wondering more than once if they'd even put him inside at all. And when they kissed, they tasted only the cum that had been pumped into their mouths. 

Maybe it was the rutting, maybe it was this marring of everything they'd been, but Sabrina felt them snap almost at the exact same moment. 

“Don't bother finding replacements,” Ash grunted, “We're leaving tonight. I'm sending you two home to my parents.” 

Ash's mothers had a thing for twins, so it felt right to give these two to them as a gift. They weren't even sure what Ash meant by this, but nodded mindlessly nonetheless as they were drilled from either side. 

Finally, Ash groaned, unloading into Tate, who did the same into Liza, both twins going limp between the two of them. 

They were out cold, and by the time they woke, they wouldn't even be in Hoenn. They'd never battle nor see their gym again. 

Ash, meanwhile, would be taking his group elsewhere. He wasn't as satisfied with Hoenn as he'd been hoping, and hoped that Sinnoh would be much more fun~


	14. Chapter 14

Chapter 13

Ash and his harem walked into Hearthome City. 

They'd been in Sinnoh for less than a day and he already had three new pokemon; soon to be four. Of the pokemon he already had, he only kept Pikachu, Bulbasaur, Charmeleon, Grovyle, Kirlia, and Milotic with him, not wanting to make travel more difficult for himself with a larger group. 

As you could only have six pokemon at any given time, the others he 'caught' wouldn't be able to be held in pokeballs, so the rest were sent back home to Kanto. The first new pokemon he'd found was a Luxio. 

She looked tough, and it had been a tough fight against Ash's Pikachu; though he ultimately ended up winning thanks to hard trained skill and speed. Despite knowing how it would go already, it was still impressive to watch the smaller mouse like pokemon defeat the larger electric feline. 

As she was defeated, Pikachu seemed to eagerly call dibs on her, which Ash allowed as a reward for doing so well, holding her while Pikachu thrust into her cunt, rutting her until we submitted willingly, at which point Ash joined the fun, fucking her throat to spitroast her with his Pikachu. 

Ash had been in desperate need of a flying type for quite some time, so when he found a Staravia flock competing against one another, he couldn't believe his luck. 

He looked over them for awhile before settling on one. She was strong and had a lot of spunk, but Ash was also able to sense that she was much more submissive than she looked. Sabrina confirmed this with a quick mental read and Ash's mind was made. 

It took some waiting for her to be far enough away from the flock for him to safely grab, but once he did he went right for it. 

He snatched the flying type and pinned her down, slamming into her avian cunt without mercy, pumping into her with all the brutality he was known for by now. 

He enjoyed how soft the Staravia's fluffy feathers were against his body as he plowed her into the dirt; enhanced the pleasure for Ash. It didn't take long to break her down, her submissive side winning out. Soon the bird pokemon was Ash's, just like all the rest he'd plundered; screeching as she passed out from the pounding. 

The last of the three was one he didn't fuck; sending a wave of shock through the harem. 

He'd found the Chimchar being beaten up by group of Machop when they found him. The Kirlia dispatched them with ease on Ash's request. Ash picked the Chimchar, comforting him as he tended to him with healing items. 

When he'd seen the small fire type getting attacked, it had brought back memories of his days being bullied as a kid. He felt a... connection to the Chimchar, and wanted to help him, not dominate him. 

So unlike the others, he wouldn't break him, wouldn't fuck him at all. Not until he was strong; and even then not until he actually wanted Ash to do so. 

That first night when they camped in the woods, Ash had found an egg. He brought it along, wondering what would hatch from it; none the wiser to how the aura and energy around him would be influenced. 

Finally the group was entering Hearthome City; and within minutes of entering Ash came to a stop as his eyes fell upon a woman and her blue haired daughter. 

The harem could tell before they even saw who he was looking at that their master had found his next targets.   
(

* * *

)  
Dawn and her mother Johanna woke up groggy and confused. They were in a hotel room, and they were missing their clothing. 

The last thing they remembered was joining the nice boy they'd met while out shopping for drinks. How they'd gotten from there to here they couldn't begin to guess. They could only assume as panic began to set into both of them that he'd not been quite as nice as he had seemed at the time. 

The harem was on them in an instant. May and Misty moved between Dawn's legs, tongues working together on her pussy while nearby her mother was grabbed and double penetrated; Richie taking her pussy and Max her ass. Sabrina telekinetically fucked the two boys with dildos, assaulting their asses as they rutted Johanna together. 

Dawn, briefly paralyzed by a cocktail of fear, confusion, and shock, began to cry out for help. She saw Ash nearby, on the bed pounding into Anabel's ass. Her ass was beet red, and he looked to have been at it for awhile. She called out to him, pleading to be freed; only to silenced by May and Misty kissing her forcefully. 

“Sorry, its too late for that,” May said, “Master has picked you. Just surrender now and you'll be happy in your new life~” 

Dawn looked at the broken women with horror, fear spreading through her at the same rate as the pleasure from them fingering her. She was remarkably sensitive it seemed, the girl cumming from their actions in spite or perhaps because of her terror. 

Misty smirked, “You won't last five minutes~” 

Ash grunted, unloading into Anabel and sliding out, letting her rest for the time being as he approached his new prizes. 

He gave May and Misty each a smack on the ass. They moved their hands to give their master full access. He licked his lips as he looked down at the terrified girl before him, shaking from the release as well as the fear. 

Her eyes widened as he kissed her, then widened more when she felt his thick cock ramming into her without warning or mercy. She screamed in the kiss as her body clenched like a vice, cumming instantly. Ash looked at her, somewhat baffled at her cumming from a single thrust. 

“How sensitive are you?” He questioned with a laugh, Dawn not replying as she attempted to keep her face covered; but it was in full display as he began hammering into her faster, overwhelming her sensitive body. 

As he did so, Misty went through Dawn's stuff and found a picture of her and a red haired girl. They were kissing and looked happy together. 

“Who's that?” Ash asked as he pounded her. 

Dawn grit her teeth, unable to stop crying out from the fucking but surprisingly able to keep the words in. Ash snapped, Misty and May going to Dawn's chest. 

They bit down on her nipples, tugging hard as Ash continued to pound into him. It was too much, Dawn screaming out. “Z-Z-ZOEY!” 

Over the next few minutes of painful, overwhelming pleasure/pain torture, they got Dawn to admit that Zoey had been her best friend since they were kids, and they'd been dating for awhile recently. 

A malicious grin spread across Ash's face as he began ramming harder into Dawn. “She looks fun~” 

Terror gave way to the purest dread Dawn had ever felt at these words, tears rolling down her cheeks as she begged with everything she could muster, swore she'd do anything for him, be anything for him if he didn't do anything to Zoey. He agreed, promising that in exchange for being his slut, Ash wouldn't lay so much as a finger on Zoey. 

He was lying of course, he wasn't about to let a pretty girl like that slip through his fingers. But Dawn didn't know that. 

It wouldn't matter; by the time he found Zoey, Dawn was too broken to argue or even care. He lifted her legs to put her into a mating press and proceeded to utter shatter her. He didn't stop for an hour, which while long in general was surprisingly small for Ash. 

He hadn't even needed to take her ass, the girl was so sensitive that she was already gone. Barely conscious with cum leaking from her poor abused cunt, Ash left Dawn and went to Johanna, who was utterly plastered in Richie and Max's cum. 

He slapped his cock down on her face, “You belong to me now, so suck. Show your daughter how good of a whore you are for me~” 

She wasn't fully broken, but her resolve had basically been erased; the boys and Sabrina fucking her for the entire hour Ash had spent on her daughter. Johanna did as she was told, taking Ash's rod into her mouth and sucking; working his cock with her tongue. 

He moaned, surprised by her skill. As a younger woman she had been sluttier than she liked to admit, having given that up upon becoming a mom. 

With her mind and body so frayed though, that part of her was coming back to the surface. Thats why when she saw Ash pull away to start fucking her, she asked him to go for her ass instead. 

He grinned, moving to line up to her ass instead, slamming in with a smack to her ass. He'd always had a fantasy of fucking his mothers once he'd become worthy of doing so, and rutting Johanna's milfy body was helping me relish that fantasy. 

He brought Dawn over, having her make out with her mother as he hilted himself in her ass, had her suck on Johanna's tits, eat Richie's cum from her cunt. They dove deeper and deeper into debauchery as he broke them, loving every minute of it. 

They spent the rest of the day initiating the two into their new lives; Ash already making plans to hunt down this Zoey girl.  
(

* * *

)  
Ash and his harem were on their way to Eterna City the next day for the grass gym leader Gardenia. 

But why settle for a gym leader when you could have a champion? On his way to Eterna, they passed a woman that stopped Ash in his tracks: Champion Cynthia. 

She had been undefeated for ten years, and recently a rumor had popped up that whoever was first to defeat her would get her as a prize. 

Knowing this, Ash had his pokemon in intensive training an hour later. He would not be leaving Sinnoh until he had her, no matter how hard they had to work.


	15. Chapter 15

A week had passed since the sight of Cynthia had set ablaze a fire inside of Ash. 

He knew of her power and knew he needed to train harder and be more ready than he had ever been before. 

His harem knew how hard he worked with his pokemon, but had never seen him work so tirelessly, cutting back even on using his harem for pleasure as he dedicated most of his attention to getting his pokemon up to snuff. 

They'd all grown, but in power and in mindset. The Chimchar Ash was so careful with had grown much more comfortable with the group, but still seemed to be quite freaked out by the idea of sex, particularly of humans and pokemon doing such a thing. 

Ash stood by his statement not to fuck the fire type unless he actively wanted it, but did encourage the fire chimp to watch as he fucked the others, as he broke them. 

He considered it a form of training, bonding with the Chimchar as it gradually began to develop desires similar to Ash's own; both for the other pokemon and the human women as well. 

Seeing this, Ash encouraged him further by making him the first to drink from May, who's now massive tits had finally started producing milk regularly. 

Dawn and Johanna had integrated into the group fairly easily. Dawn was right in place next to May, Misty, and Anabel, to the point that Ash felt like he was collecting pieces of a collection.

And everyone seemed to like Johanna whether they were broken or not, her milfy body drawing the eyes of even those who'd brains were practically vestigial. 

Richie in particular found himself drawn to her; not that he dared go near her without asking first, such a concept wasn't one he could fathom at this point. 

Seeing the growing size of his harem, and Johanna's motherly body, made Ash wonder which of his pets would make good breeders. He would of course have his first child with his lovely wife, but it was only natural that the pets would be used for baby making as well at some point. 

He hadn't yet come to a decision, being so focused on his training. He'd put a lot of focus on his Charmeleon to try and evolve him, as well as his Staravia. The latter seemed to have drawn the Chimchar's eye, Ash noticed. 

He couldn't blame the fire type. He knew from experience how good the large bird pokemon was to fuck. 

The closer they got to Eterna City, the more and more Ash and Sabrina got this feeling of being... watched. Sabrina confirmed the feeling when Ash brought it up, as she could feel it not only physically, but psychically. 

They didn't mention it often, as it only seemed to be watching, and they knew the legends of mysterious pokemon that kept their eyes out over travelers. They couldn't know at the time just why they were being watched, nor how many truly were watching. 

“Should we do something about it?” Ash asked between groans one night as he pushed deep into Sabrina's tight, lovely ass. Sabrina moaned, shaking her head. 

“They're only watching for now. They're powerful to be sure, but they seem more curious than malicious. Leave them be until something happens.” Sabrina explained as she worked her hips to milk her husband's rod even better. 

Ash shuddered, moaning as he thrust against her. He trusted his wife, and even if he didn't she was too good with her body not to melt away any other thoughts he was having at the time. 

So they continued their fun, sparing no further thoughts to the three entities watching them, two out of not but curiosity; but the third with a more genuine interest...   
(

* * *

)  
A few days had passed and Ash found himself balls deep inside of Gardenia. 

He hammered into the grass gym leader missionary style, his Roselia riding her face happily as his Bulbasaur's vines abused both her own and the Roselia's assholes. 

Gardenia couldn't see much from under the Roselia, but could occasionally catch glimpses of Ash's Grovyle fucking her Roserade like a cheap fuck doll. 

And despite her begging and pleading and sobbing, Ash, Sabrina, and Gardenia knew on some level she was loving every second of it. 

She'd actually been difficult to defeat, as Ash had opted on Sabrina's suggestion to use only fellow grass types against her. 

Poison moves helped but in the end it came down to Grovyle's speed and raw power. 

As it often was, Sabrina's suggestion played into the gym leader's hidden kink. 

While it was news to no one that she liked grass types, Sabrina had found that she liked them a bit more than a gym leader generally loved their preferred type. 

Sabrina wasn't about to suggest that her whole career was her indulging in a fetish, but Gardenia certainly hadn't become a grass gym leader for the scenery alone. 

Watching the grass type on grass type combat must have been like porn for her, as Ash could see the puddle her wetness was making from across the arena. 

Realizing what was happening, Ash needed only snap as the battle ended to order his Grovyle to pounce on the defeated Roserade, lifting her already sore body and pounding her against one of the nearby trees. 

Ash was on Gardenia in moments, the gym leader trying to fight him off but unable to. She was too off guard from the shock of it and from her own arousal, to say nothing of Ash's own physical prowess. 

“How often do you let grass types fuck you~?” He questioned as he started stripping her, “Do you only use your own team or do you whore yourself out to wild grass types to~?” 

She tried to argue that she'd never fucked a pokemon before, that she thought he was a disgusting pervert, but she knew how little weight her words held with her shorts soaked through before he'd even torn them off. 

Her body betraying her, and her mind half convinced this was all a dream, she gave in, undressing from the waist up and letting Ash have his way with her. Ash could feel how happy her body was for it when he had his grass pokemon join them, instantly squeezing even tighter around him. 

But he wasn't here to grant her wishes. He was here to break her. So even as the plant pokemon satisfied her fetish, he slammed to the base inside of her, forcing her to take every inch. She screamed against the Roselia as Ash pounded her, making his own efforts the only thing she could have possibly focused on. 

Her back arched as she took every inch, cumming hard repeatedly as he kept going. He wondered if she even noticed when the grass types had stopped, if he'd broken her so fast she didn't even realize that after the first ten or so minutes it was just him plowing her like a field. 

Given that by the hour mark she was begging him to breed her, he could only assume something along those lines. He smirked as he stuffed her, unloading into her hot cunt with a sigh of pleasure. 

To his surprise though, rather than collapse, she simply moved onto her stomach, lifting her hips and shaking them, “More.. fill me husband.. breed me~!” 

Her tone was far off from its usual, her break cracked like an egg. He gave a glance to Sabrina to show his amusement as he continued fucking the grass girl. And while she returned the look as she rode Richie with her ass, inside she felt something bubbling. 

It felt like jealously but she didn't understand why. She'd watched her husband fuck dozens of others by this point, helped him do so and done so herself. 

Why was this girl upsetting her? Sabrina grew slightly flustered at realizing it was her calling him 'husband' that was setting her off, even if she was too far gone for the words to carry any meaning behind them. 

She still couldn't believe sometimes how deeply she'd ended up caring for him. What a time to be alive.. 

They'd only be in Eterna City for a few more days before setting off for Snowpoint; and a certain red haired coordinator..


	16. Chapter 16

Ash and his group ended up staying in Eterna city for nearly a month; mostly training but also enjoying Gardenia. 

Being so easily bent to Ash's will and desperate for him to breed her had been fun, but it was time to set out now. 

More harem members to claim, pokemon to catch, and training to do. Like with some others he'd broken, Ash understood it would have been a bad idea to just uproot Gardenia from the gym, as it would raise quite a lot of questions and probably result in a full on investigation of some kind. 

As time to leave drew near, Gardenia asked if Ash would leave his Bulbasaur with her for the time being; for obvious reasons. 

He allowed it in exchange for a shiny stone so he could evolve his Roselia; which she happily coughed up. And with that he was ready to go. 

“I'll be alright without you for now, soon I'll be with child~” Gardenia purred, eyes just as glazed over as when he'd first broken her, “Until you return husband~” 

Everyone but Ash tensed up as she said this, someone worried Sabrina would snap and go on a rampage of some sorts. 

Thankfully she seemed to have enough self control to simply bring up her issues with Ash after they laughed. Ash gave her a loving smile as he pulled her against him, “Don't worry Sabrina. 

She can call me whatever she likes, but you're my real wife~” He assured her. Sabrina smiled, leaning in to kiss her lover before they set off on a long trek towards Snow Point City.  
(

* * *

)  
The trip Snow Point City was, while not the longest at only three weeks, certainly the most dangerous travels Ash and his team had had to bare through. 

The mountains, rough terrain, and a chilling blizzard all acted as road blocks between them Snow Point, forcing them to take refuse in whatever small town shelters they could find along the way to Snow Point. 

They arrived early in the morning, looking frozen half to death as they made a beeline for the inn so they could finally relax and warm the fuck back up. 

Happily it didn't take too long to warm up and calm down from the trip once inside, and slowly everyone was recovering. As they did so, Ash couldn't help but perk up at seeing someone vaguely familiar. 

“Is that..” Ash pointed out a redhead woman, Dawn turning and simply nodding. 

“That's Zoey.” Ash grinned, instructing Dawn to go over and 'run into her coincidentally'. 

Dawn nodded, getting up and heading over. Sabrina connected to Dawn's mind. If the two had been as close as it seemed, Zoey would likely notice that something was off if Sabrina didn't intervene, fetching old memories and drawing up old emotions temporarily so her responses to Zoey would appear at least halfway genuine. 

The hardest to do was to suppress Dawn's instincts relating to Ash, that way she could tell Zoey about them in a way that didn't trigger any red flags. 

With Sabrina's help, Dawn managed to talk with Zoey just like they'd used to, the poor girl none the wiser to what was happening as Dawn told her about all her new friends and how much fun they had together. 

Some weak, beaten, forgotten part of Dawn's soul felt guilty, wanted to grab Zoey and tell her to run. But it was so beaten into shape that Sabrina didn't even need to suppress it, Dawn's new instincts doing that for her. 

Before long, Dawn was escorting her 'girlfriend' to one of the rooms in the inn for some fun. Zoey was happier than she'd been in months, stumbling into the room with Dawn, locked at the lips. 

They fell onto the bed, still making out heatedly. There was something... off about it.. but they'd been apart for too long, they just needed time to get back in sync with one another. 

They began stripping each other down, only growing more heated until Zoey's eyes moved to the writing on Dawn's inner thighs. 

'Property of Ash,' on one, and 'Ash's happy fuck hole' on the other. 

The barrage of questions didn't even get a chance to start as Zoey suddenly felt her entire body freeze in place. Ash entered, thanking Sabrina for her psychic help holding Zoey in place. 

Johanna and Richie followed behind the two of them. Zoey wanted to question what the hell was happening but couldn't. Luckily, Dawn explained it anyway. Unluckily, the answer was one that made her blood run cold. 

As Ash rammed his fingers into Dawn's wet cunt-an action that made Zoey instinctively attempt to break free of her psychic hold to try and save her lover, a futile effort for a number of reasons-Dawn explained. 

“Master broke me some time ago, I'm just his play thing now.” Ash couldn't help but smirk at the sheer dread and hopelessness spreading across Zoey's face; a look that grew even more intense when Dawn continued, “We can't be together, not anymore, not really. But since Master is going to break you to, we'll be around each other other at least.” 

She was cut off from saying more by Ash's pinching her clit, sending her over the edge and making her legs wobble. “Now now,” Ash chided, “Don't spoil it all~” 

Zoey raged more as she watched Ash kiss her; caught completely off guard as she felt someone's fingers pushing into her ass. 

“Nice and tight back here, must not have much experience,” Sabrina said as her fingers worked deeper into Sabrina's ass before sliding out to smack her ass roughly, “Don't worry, that'll change soon~” 

Zoey looked on in horror as Ash undressed, approaching her with his slowly stiffening member. She'd been with guys once or twice before, done things with strap-ons with Dawn before, but she'd never seen anything of Ash's size. 

She continued to struggle against Sabrina's psychic hold, only stopped in her efforts by the sudden feeling of Dawn's lips against her own. Despite the nightmare around them, being close to Dawn was still bliss. 

The key word being 'was.' As going forward Zoey wouldn't be able to think of it without thinking of the moment immediately after where Dawn pulled Zoey's hips down hard, impaling her down to the base on Ash's cock. Zoey screamed into the kiss, shaking as Ash's cock stretched her unprepared cunt. 

Tears rolled down Zoey's face as Ash began thrusting up into her, groaning happily at the feeling of her tight body around his cock. It hurt like hell, made even worse by Sabrina's aggressive fingering. 

She cried out against at a rough smack to her tits, “Nice rack, might make another milk maid with you~” Ash purred. Zoey had no idea what this meant, but could tell from the tone in Ash's voice that it meant nothing good for her. 

Zoey's body shook and tensed and burst, cumming despite Zoey's disgust with the situation; the stimulation too intense for her. 

Sabrina, more for her own amusement than any actual need, did some peeking inside Zoey's mind, finding a hidden, taboo fetish. 

Seems the redhead had actual fantasied about watching Dawn with other people before, found the concept kinky and hot. 

This was most definitely not what she'd imagined, and said fetish was probably making her feel like shit about now, but Sabrina figured it could come in handy later regardless. 

Ash was having no issue forcing Zoey to cum at the moment regardless, bringing the redhead over again and again with his powerful and skilled thrusts. 

She was approaching her fifth by Ash's count by the time Ash finally went over the edge, dumping a thick, hot release of cum into her. She screamed out as she took it, leg twitching as she went over the edge once again, tear stained eyes starting to turn glassy as Ash finally slid out of her. 

She had, for a moment, the foolish though that she could finally get a little rest. Said thought was made laughable within seconds as Ash's cock was replaced by Sabrina's strap-on of nearly the same size; Zoey's sore cunt being hammered into once again. Ash laid down on his back, beckoning for his wife to line up their new plaything. 

With a smile, Sabrina moved Zoey down, pressing the tip of Ash's cock against Zoey's ass. She opened her mouth to try and beg. She knew it would do no good, but she felt she had to try. Aside from Sabrina's fingers earlier Zoey had never had anything back there. 

To follow that immediately with something the size of Ash's cock- Ash grabbed her hips, pulling her down hard as he thrust up, impaling her on his cock. He was aided by Sabrina's powerful thrust into her pussy, forcing her down harder on Ash's rod. 

He moaned happily at forcing the walls of her unused ass apart, able to hear how much pain she was in despite how weakly she was crying out now. 

Zoey couldn't even sob anymore, the sensation too intense, too much for her to keep up with anymore. She felt like she was going to break in two; she honestly hoped she would, feeling it would be better than what was happening to her. 

Unfortunately for her, she remained in one piece, remained a toy for the two lovers to slam into without a single care for how she felt. 

It made sense to break her fully, it was a mercy in fact. She'd live in heartbreak otherwise, knowing the one she'd fallen for no longer felt anything for her truly. The only solution was to give her the same treatment. 

Nearby, watching Zoey get stuffed from either side like a worthless whore, Dawn fingered herself aggressively. With her mind broken several times over, all she could do was relish the depravity she was subjected to, a brainless smile on her face as she watched her ex girlfriend get fucked. 

Seeing this, Ash called her over. 

Understanding almost immediately what Ash wanted, Dawn happily mounted Zoey, forcing her wet cunt against Zoey's mouth. 

Zoey's tongue worked against Dawn's pussy practically against her will, more attempting to cry out for help than actually eat her out; but it achieved the same goal regardless. 

And it was there, her ass in more pain than she'd ever felt from Ash's powerful cock inside it, her cunt stuffed with thick cum and being drilled by Sabrina's strap-on, with Dawn's juices soaking her face and tasting distressingly of Ash's cock, that Zoey finally broke, the last of her willpower snuffed out. There was nothing left for her. 

Even if she could fight it there was nothing to win anymore. She gave in completely. Whatever a Milk Maid was, she accepted it, accepted that if nothing else, whatever was left of her would still be with whatever was left of Dawn. 

She didn't even respond as she felt her poor abused ass flooded with Ash's cum, simply taking it like a good little slut. 

All moved off of and out of her, Ash pulling her by her hair to his cock, “You belong to your Master now. Understood?” 

Zoey nodded, confirming it by kissing Ash's cock with reverence. He smiled, dropping her and moving to Dawn, pulling her onto his cock. He fucked her without love or care for her enjoyment, using her like a toy. 

If Zoey was still there at all she might have burst into hysterical laughter at the thought that her secret fetish was being used against her. It didn't matter anymore. 

This was her new life, and she might as well be okay with it.  
(

* * *

)  
A week had passed in Snowpoint. 

The weather had grown rougher and rougher, making leaving the city less than feasible even for Ash and his team. 

He was content to continue his training in the snow, paying extra to the inn for the long stay; and as a way to apologize for the noise complaints they got on a nightly basis. Zoey had slid into her role in the harem as easily as Dawn had before. 

She would start the process of becoming a Milk Maid soon, and spent plenty of time admiring the plump, full tits May had developed as a result. 

The pokemon seemed to enjoy drinking from May daily, and despite their size, Ash assured her that May hadn't even fully finished growing yet. She'd get bigger, produce even more, and become even more sensitive before the process finished. 

Mind you Zoey's willingness was more of a formality, but it helped; as did Zoey's kink for watching her ex get fucked by others, a kink Dawn seemed to have developed as well with Zoey around. 

The two only seemed to genuine enjoy themselves-if mindbroken slaves can be considered to ever actually enjoy or even experience anything at all-when they were watching each other get drilled by one of the others; usually Max and Richie. 

As the two watched each other get railed, the Luxio limped back in after some rough training and rougher rutting of the Starvavia, currently on her back. Ash was still out with both his Charmeleon and Chimchar; pounding the former face down into the snow while the later watched. 

The fire chimp still hadn't joined the fun, but had grown fond of watching; particularly watching Ash. Ash had been putting a lot of attention into Charmeleon over the week, as he knew that he was close to evolving and wanted to instill a sense of obedience into him before he grew too prideful for it to take. 

The Chimchar continued to watch, though it didn't seem time to for him to join yet; much as Ash wanted him to. Ash grunted as he slammed into the fire type, pounding his sensitive prostate with each thrust. 

He forced his head to turn, kissing him forcefully as he leaned over his body, hips not slowing for a second. Ash felt him grip tighter around his cock as he began to glow. 

Ash shuddered at the feeling, keeping a hold of the Charmeleon in its final moments of being a Charmeleon, flooding its ass with thick cum. 

The pokemon let out a low grown of pleasure, cumming as he evolved and collapsing into the snow as a powerful, intimidating, and completely broken and subservient Charizard. 

Ash confirmed this by flipping the pokemon over onto his back, straddling his chest with his throbbing cock slapping against his face. 

It was a risky move, as if he were even slightly wrong, the pleasures of his journey could come to a sudden and brutal end. But he was confident, and smiled as, rather than retaliate, the Charizard obediently licked and sucked at his cock. 

Looking over, he found the Chimchar still watching, gently stroking his cock from the sight before him. He smiled, enjoying the pleasure and wondering how the moment could get any better. 

As though the universe itself was attempting to answer him, there was a found like a crack and a pop, and a Riolu sprung from Ash's bag; the bag he'd kept the egg he'd found stored in. the Riolu took a combative stance, seeming energetic and ready to fight right that moment. 

Ash grinned, grabbing the Charizard's horns like handles and forcing his cock to the base inside his heated throat so he could go over the edge faster and get to the new pokemon. 

The egg had hatched, Charmeleon had evolved, Chimchar was getting closer to joining him in their sexual side of the adventure, Zoey was claimed and when he'd expressed interest in wanting to add another boy to the harem, Zoey had mentioned pain in the ass of a boy she knew in Veilstone that could certainly do with some breaking. It was perfect. 

“This region is a gold mine~” He moaned as he filled the Charizard's throat.


	17. Chapter 17

Candice was perhaps one of Ash's easiest catches in terms of gym leader girls. 

No sooner had the battle ended was Candice on her back, Ash sinking his pole-arm of a cock into her tight, unprepared cunt. 

She was a nice, peppy girl and her energy was somewhat infectious; making Ash not want to wait. He tore her clothes from her body, holding her against the cold ground as he sawed into her pussy. He could feel her trying to resist, but it wasn't doing much to help her. 

Soon her eyes were fully glazed over, tongue lulling out with a blissful smile as Ash used her like a cheap sex doll. The battle had been something of a joke. 

He'd been intending to use both of his type strong pokemon, Chimchar and Riolu. But he ended up not needing to; the fire chimp burning through the ice gym leader's team with surprising ease given first appearances. 

The only thing to not be one or two shot was the Abomasnow, who was too bulky for the Chimchar, strong as they were, to actually beat. That is, until he evolved mid-battle. 

As a Monferno, he had easily finished the battle, bringing down the Abomasnow. He panted, grinning with victory. He watched as Ash pounced on and began fucking Candice, growing stiff as the sounds of skin slapping against skin filled the room. 

Ash, knowing what Monferno wanted, snapped his fingers. May sauntered into view, her massive milk maid tits swaying with each step. 

The fire chimp pounced on her without further warning, pinning her to the ground as he began sucking on her plump breasts, drinking from her. 

Ash smiled as he watched this, watching the fire type sink his member into May's cunt as he drank from her. He flipped Candice over before continuing to drill into her. 

“I think.. you'll make a good caretaker for my family. When the time comes of course.” 

Candice only responded with hazy groans at first, then a yelp as Ash struck her ass roughly. “Y-yes s-sir.” She managed to force out passed her lips as she continued to take his cock deeper than she'd ever taken anything, wincing as he pulled her back buy her hair to fuck her harder. 

“I-I'm yours~” Ash smirked, continuing to fuck the broken ice type gym leader, feeling her body squeeze around his cock as it simply gave up on anything other than serving its new master. 

He grunted, unloading into her, “Certainly are~” He confirmed. As he left her there, ordering Max to enjoy her as he went over to May and his Monferno. As Max sank himself into Candice's ass, Ash pushed a finger into the fire type's to gauge their reaction. 

The Monferno grunted and moaned, hips continuing to pump into May as he felt Ash's fingers probe deeper into his tight, virgin hole. 

After a few minutes of fingering to prepare him, Monferno felt Ash's tip press against the puckered hole. Looking over his shoulder, he could see that Ash was actually waiting for permission. 

With a smile, he nodded. Matching his grin, Ash slowly pushed into the Monferno, moaning with him as he continued to fuck May; slowly feeling Ash's cock stretching his tight, heated walls more and more. 

He was tender and slow, actually wanting him to enjoy it unlike so many others. And the Monferno was surprised by how much he enjoyed it, hips bucking faster to take more as he continued to plow May. 

Ash grit his teeth as he felt the Monferno's hot, tight ass squeeze around his cock as he came into May. Ash moved back, bringing the Monferno with him as he stayed inside his hot, tight body. He stood up fully with the fire type still on his cock. 

Unable to resist any longer, Ash let loose, hammering up into the Monferno; who's moans began echoing in the gym. Ash grunted as he stuffed the fire chimp; but unlike the others, was surprisingly caring with his motions. 

Even as he let himself go all out, his movements were not cruel. Dominant but not domineering; maintaining his role as Master and the Monferno's as slave, but deliberately not breaking the Monferno. He wanted to train the fire type into another alpha; someone like himself. 

He turned the Monfero's head, kissing him warmly as he hilted inside the fire type. When they came, they went over the edge together, groaning in shared pleasure. And just like that, they were done with Snowpoint and ready to move on. 

Their next destination would be Veilstone.  
(

* * *

)   
A week had passed now. A boat had been needed to escape the hell of ice and snow. Finally, they'd freed themselves from the poor weather. 

Rather than heading directly to Veilstone, Ash had the group take a slight detour to the south-west of the town; to Lake Valor. 

Since arriving in this region Ash had been being spied on by ever more curious beings. It was so intense that Ash could sense it without Sabrina's help, and he felt it was high time he got to the bottom of it. 

He stood at the edge of the lake, waiting. Happily, he didn't need to wake long before the three appeared before him. 

“Finally done just watching are you?” He asked the three with a smirk as the Lake guardians appeared. Azelf, Mesprit, and Uxie looked to one another, then back to Ash, grinning. 

Indeed, they were.


	18. Chapter 18

Moans filled the air as Ash grunted, hammering into the lake guardian Azelf. 

How fucking lucky he must be to find himself in this position, with not one but three legendary pokemon laying submissive before him, he couldn't begin to fathom and didn't give a fuck. 

They had been watching him since his arrival in this region, observing every action he took with all of his conquests; so he had known from the moment of their arrival that they all knew what they were getting into when they appeared to him finally. 

All three had developed feelings for the young man, though of the three Azelf seemed to have the least control over her emotions. She'd rushed in, bringing Ash into a loving, heated kiss.

Ash held the legendary's small body against his own, gently feeling her as a simple kiss became a passionate make out. The other two watched in fascination, slowly beginning to play with their own bodies as they once again watched Ash. 

Then, quite suddenly, Ash pulled Azelf down, impaling her onto his massive rod; intending to bury himself to the base inside her in a single, powerful motion. 

She let out a cry as her eyes widened, her small body only able to take two thirds of Ash's cock inside as she squeezed around it. Ash groaned, beginning to work her body up and down, using her like an onahole. 

Azelf's moans only grew louder with each powerful thrust into her small body. Even not being able to take all of it, the psychic type legendary was in bliss as she felt her body being used by the human they'd been watching for so long. 

Her tongue lulled out in ecstasy as Ash hammered into her, her two long tendril like tails wrapping around the base of Ash's tail and starting to stroke so she could tend to the the rest of Ash's cock. 

He was surprised how lucid she remained even with him going all out. Never underestimate a legendary he supposed. 

Nevertheless, Azelf's body went limp after a scream of pleasure as Ash filled her several times over with a powerful release, bloating her. She slumped down the ground, excess seed leaking from her. As soon as he looked away from Azelf he saw Mesprit. 

Seemed she was fairly overconfident in herself, floating in a position as though she were on her fours, hips wiggling for Ash as she gave him a cheeky smirk over her shoulder at Ash. Wanting to rid her of this confidence, Ash didn't bother with the tenderness he'd allowed Azelf. 

He grabbed Mesprit by two of the hair like growths on the pink lake guardian's head, pulling them back hard as he thrust forward, sinking himself into her as rough in not rougher as he had into Azelf. 

Pleasure flooded her senses immediately at a greater intensity than she was ready for. She could feel every inch forcing into her, stretching her inside, the heat of his cock practically melting her mind. 

Despite her confidence, she barely lasted half the time as Azelf; though Ash kept going even after she'd seemingly lost consciousness, using her body so she would learn her place; a unique pleasure with her being a legendary. 

Being innately the most shy, and having just watched what confidence would result in, Uxie was blushing and hiding her face as Ash approached her, sitting on the ground with her legs spread. 

She didn't realize until too late that this behavior actually got him the hardest out of the three of them, and he pounced on her like a hungry Houndoom; drilling her into the dirt with force and vigor that made her screams eclipse her fellow guardians by quite a bit. 

She gasped at the lewd bulging of her stomach caused by Ash's cock in the moments before her eyes started rolling back from the intense pounding. A

sh felt fairly confident in his abilities, and was glad to have captured three legendaries. He was surprised, if not so surprised, when mere minutes after their first rounds the lake guardians were not only back up again, but unbroken. 

Hell Azelf was already up for round two. Ash wasn't sure if their mental strength was to do with them being psychic types, them being legendaries, or a combination of both. 

He supposed he couldn't break them as such, even if they were submissive to him. Angry though this made him, he understood that there wasn't anything for it; and soon Azelf was riding him again to placate him with pleasure. 

Despite his being unable to properly break them, tonight may well have been his most productive night of harem building yet.  
(

* * *

)   
Over the next few days the harem developed in several ways. 

While Azelf seemed to remain attached to Ash at the hip-quite literally in times-Mesprit and Uxie seemed more keen on Sabrina and Anabel specifically. 

All three were loyal to Ash, but Ash seemed to be the only male Mesprit specifically cared much for, enjoying the female form far more in all other cases; though it seemed to be Sabrina's psychic power that got Mesprit the most wet. 

Why Uxie was so obsessed with Annabel Ash wasn't fully sure. He could only guess that the shyest of the three lake guardians had some secret sadistic fantasies she finally had an outlet for. 

It wouldn't shock him; it was always the quiet ones after all. But the guardians were far from the only development. 

His Luxio, Staravia, and Kirlia, had all recently evolved; all through sex, as Ash found it the most fun and suspected it might lead to them being even sluttier innately as a Luxray, Staraptor, and Gardevoir. Not that the latter needed it. 

Being literally linked to his mind and emotions, the Gardevoir was only ever going to become a masochistic sex toy with no purpose but to be used. She could technically have used this empathetic link to become similar to Ash in personality, but her powers had correctly deduced that Ash wouldn't want someone like her in the roll of apprentice. 

Even as Ash enjoyed her newly evolved, beaten red ass, he found it perplexing and delightful to have a pokemon who's natural abilities broke her for him. But that also wasn't the end of the strange develops over the course of those few days. 

He'd begun noticing.. for lack of a better word, independent behavior among his harem. 

Nothing big, no one ever disagreed with Ash and he was quite certain they'd talk off the edge of a cliff if he ordered it, but more and more he began to notice them actively choosing to do things without needing to be ordered to. 

Richie and Misty seemed to go at it more frequently, rutting rough and seemingly passionately. 

More blatantly was Dawn and Zoey, who could be found fucking like Lopunny in spring whenever they weren't specifically ordered to do otherwise, as though pretending to still be the lovers they once were. 

Ash wondered for a time he needed to re-break them, reestablish to them all who was truly in charge; but Sabrina stayed his hand. 

“Its fun to watch them pretend,” Sabrina said with an amused smile, “Its no real harm. They still obey without hesitation.” 

Ash agreed, though couldn't help but wonder if he was only doing so because it had been suggested by his lovely wife. He chuckled to himself, figuring that even if by some miracle of the gods they all fully became themselves again, if it amused Sabrina to watch, it might be worth it anyway. 

It would let him break them all over again anyway; so he felt she was right. Hardly an issue. As he walked, it occurred to Ash that he had only really claimed Zoey, Dawn, and Dawn's mother from this region. He had broken others yes, made them his own; but they all had to stay here, at least for the time being. 

He wanted another to bring with him away from the region, one more tight, fresh hole to mold around his cock. And as if granted by Arceus, a relatively cute little blonde boy by the name of Barry crashed into Ash, having seemingly been in a dead sprint and not looking where he was going. 

As Barry got up from the ground, far from apologizing, he demanded a pokemon battle from Ash. Ash smirked, the gears turning in his head. 

“Sure thing. In fact, I'll do you one better.” Ash beckoned to his harem, the girl's all posing as sexy and sultry as they could, reacting to mental orders relayed to them via Sabrina. Barry blushed deeply, eyes briefly becoming hearts as he practically began drooling. 

“A wager. If you beat me, you can pick any of my girls here and fuck them however you like. And if I win-” Ash was cut off by Barry sending out his first pokemon, an Empoleon. 

“No need to tell me,” Barry assured him, “I don't lose!” Ash was half tempted to test that theory with his normal pokemon; but figured that the three legendaries he'd just acquired would make a far better lesson in not only humility but utter humiliation. 

The lake guardians proceeded to do to Barry's team something equivalent to what horny Machamp would do to a rattata; his entire team of six laid out like nothing in as many minutes if not less. 

Barry stared in utter shock, his pride as roughed up as his team and his dreams of lust shattered. 

He sighed as he recalled his pokemon, starting to ask what it was he was meant to have wagered. This time, though, it was his turn to be interrupted. 

A blast of psychic energy send his clothes flying off his body in tatters as his now naked body was bound by psychic force. 

As Ash was undressed by his harem, May and Zoey dropping to their knees to stroke his cock to feel hardness, Barry realized the degree to which he had just fucked up. 

“W-what's going on? P-please don't do this!” Barry pleaded as Ash approached, throbbing cock standing at attention. 

He yelped in pain and surprise as Sabrina tied a belt around his cock. It wasn't so tight that he wouldn't be able to feel through it, but tight enough that he wouldn't be able to cum no matter how badly his body tried to. 

“Sh~” Ash purred as he moved behind Barry, groping his soft ass, “Just relax and be a good girl for me~ I'm sure you'll enjoy things better that way~” 

“W-what? What are you talking ab-AH!” Barry cried out as he was suddenly bent over, the ring of muscle that was his entrance forced apart to accommodate Ash's thick cock. 

Ash grunted in pleasure, pulling Barry's arms back as he began rutting into him, stretching him more with each thrust as he worked his way deeper and deeper into his new 'new'. 

Tears welled up in Barry's eyes at the intense pain and forced pleasured as Ash used his ass. He begged Ash to stop as he sobbed. Initially Ash just continually struck Barry's ass as punishment for this. 

When his entire Ash was bright red and Barry still wouldn't stop, he looked to Sabrina, “Mind helping me teach this bitch her place?” 

Sabrina nodded, approaching Barry from the front and silencing his pleas with her strap-on. He gagged as his head was forced down, his throat invaded as Sabrina thrust the faux cock to fuck his face. 

Ash and Sabrina spit-roasted Barry together, moving in perfect harmony; but they would by no means be the only ones to fuck Barry that afternoon. 

When Sabrina had had her fun fucking Barry's face, Max, Richie, and the Monferno all got turns using his throat as well; them able to cum afterwards and finally start matching the seed that Ash had been pumping into his ass. 

Ash changed position at some point into a sitting position, bouncing the blonde on his cock as his own bound member was left exposed for the girls of the group; all of whom seemed to get something of a kick out of using him like a toy while he writhed in agony, cock and balls throbbing with the desire to cum with each girl who rode him or toyed with his sac, only for the release to be impossible every single time. 

His swollen cock was so backed up and desperate part of Ash worried it would actually break through the belt or just become permanent damage before Barry broke. 

But of course, Barry's mind went well before his body. Finally, he cried out that he'd do whatever Ash wanted if he just let him cum. 

“Anything huh~?” Ash grunted as his cock hammered against Barry's prostate, only worsening Barry's desire to cum, “Even swear to be a part of my harem, to an obedient girl for me for the rest of your life~?” 

“YES! ANYTHING! I-I'll be a girl for you, I'll be yours forever, I swear!” Barry screamed out, the last of 'her' sanity breaking down as the physical needs broke her down. 

Ash brought Barry down to the base, tip grinding hard against their prostate as he reached around, gripping Barry's turgid and desperate cock hard and stroking it aggressively; tormenting his new pet for as long as possible as several of the girls of the harem moved onto their knees in front of them. 

He let it last just long enough to make Barry wonder if he planned to ever let them cum before he finally undid the belt. 

He unloaded into the blonde once more as Barry went over the edge harder than they ever had before or likely ever would again; already overfull asshole getting one more load as the largest Barry would ever experience erupted out over all the girls of the harem, including herself. 

Barry collapsed to the ground in a puddle of her own release, Ash's leaking from her worn asshole as Ash began picturing the kinds of clothes they'd get for their new girl. 

He smiled happily at the thought. A new harem member, he would be challenging Maylene soon; life was good.


End file.
